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White steeples towards crisp blue skies, wonderful autumn colours and fall foliage such as you wouldnโt imagine, recent lobster rolls, REAL maple syrup โ New England conjures all types of cozy associations! And a few not so cozy, like nice white sharks, witch-hunts, whaling, and rabid sports activities followers (donโt fear, they donโt assault until youโre sporting a Yankees hat). Whether or not youโre planning a fall getaway or a summer time trip, the shoreline and mountains of New England make for one really unforgettable street journey!
My household hails from New England way back to the Mayflower, and for the primary 3 years of my life, I used to be a full-fledged Bostonian โ accent and all. I spent fairly a little bit of time visiting Massachusetts rising up: staying with household in Cape Cod, visiting my sister in school in Boston (Wellesley), briefly attending faculty in Western Massachusetts (Mount Holyoke), and interning for one sunny summer time in Newburyport. However Iโve but to finish a full-fledged New England street journeyโฆ which is why I tapped journey author and Massachusetts native Anna Laird Barto to create the right itinerary!
This New England street journey itinerary visits Massachusetts, Maine, New Hampshire, Vermont, Connecticut, and Rhode Island and captures as a lot of New Englandโs appeal, magnificence, historical past and quirkiness as potential in ten days โ with loads of stops for witches, ghosts, and lobsters alongside the way in which. Take it away, Anna!
Psst: Planning on exploring extra of the East Coast? Check out a few of our different posts!
New England Highway Journey FAQs
As a result of the entire of New England is relatively small โ in regards to the measurement of Arizona โ outsiders usually underestimate the variety throughout the area. After I inform folks out west Iโm from Massachusetts, they instantly assume Iโm from Boston.
Really, my hometown of Amherst is nearer to Vermont. And nobody on this a part of the state seems like JFK or an Irish mobster from a Scorsese movie. I prefer to assume that weโre higher drivers too.
Apart from the place youโll discover the worst drivers in New England (ahem: Boston), there are a couple of extra stuff youโll must know earlier than taking your New England street journey.
The place ought to I fly out and in of?
This itinerary begins and finishes in Boston. Boston Logan is among the busiest airports within the nation, with continuous service to and from a whole bunch of locations worldwide. Itโs additionally only a 10-20 minute drive from downtown, relying, as all the time, on the visitors!
The place ought to I lease a automobile?
All the foremost car rental companies function out of Logan. However be forewarned that parking areas are essentially the most coveted actual property within the metropolis. For those who keep anyplace close to downtown, you’ll pay to park, usually between $25-$39 per day.
An alternative choice is to take a Lyft to your lodge and decide up your automobile the following morning, both at Logan or a downtown location. You receivedโt want or need a automobile to get round downtown.ย
- Journey Tip: Booked your flight and rental car but? We advocate utilizing Kayak to price-compare offers and dates to save cashโฆ so you possibly can spend extra on meals throughout your journey (#letsbehonest).
Whatโs one of the best time of the 12 months to take a New England Highway Journey?
Go within the fall when you can, and put together to be spoiled for fall anyplace else for the remainder of your life. Itโs not solely in regards to the leaves, which morph into each possible tone of gold, orange, purple, and brown, however the crisp, clear air and the solar burning by way of the morning mist.ย
The farther north you go, the sooner the leaves change colour, though the precise timing varies as a result of issues like common annual rainfall and temperature. Usually, peak colours seem in Maine and northern New England across the finish of September, whereas Connecticut could not see peak colours till nearly Halloween.ย
For those who canโt swing a fall journey, summer time is an in depth second. The climate might be downright sultry, particularly in southern New England, however the ocean, seashores, and spring-fed swimming holes are chilly and refreshing! Plus, summer time is the best time of 12 months for a scrumptious lobster roll!
Issues To Know Earlier than Taking a New England Highway Journey?
- In New England we’ve โhighwaysโ not โfreeways.โ We normally seek advice from them by quantity: 495, 91, and many others., apart from Route 90, which is solely โthe Pike.โ This itinerary avoids the Pike as a result of itโs stuffed with vans and potholes.
- Look ahead to deer, mooseโฆ and wild turkeys!ย Flocks of untamed turkeys are frequent even within the suburbs. Once they resolve to cross the street, spare your horn: no energy on earth could make them hurry up.
- Drive occasions can differ dramatically relying on visitors, particularly round Boston.ย We did warn you in regards to the drivers in Boston, proper?
- Donโt be fooled by our gruff exterior. New Englanders may not appear pleasant, however weโre secretly dying to inform you all about this place we name house. Simply donโt get my dad began on the geology of Cape Codโs Kettle Lakes!
Whatโs the historical past of New England?
Everyone knows the model that we discovered in class: in 1600-something, a bunch of English Puritans in search of non secular freedom (and fewer taxes) sailed throughout the ocean within the Mayflower (together with Liaโs problematic ancestor, Miles Standish) and arrived at Plymouth Rock, near demise and with completely no clue what they had been doing. Because of the generosity of the Indigenous peoples, they thrived sufficient to subsequently take over your complete continent. The remainder โ witch hunts and revolutions and all, see Hamilton and The Crucible for particulars โ is historical past.
However what in regards to the historical past of New England BEFORE the arrival of the Mayflower? 1000’s of years earlier than the US (a lot much less the Crimson Sox) declared itself a nation, this northeastern tip of Turtle Island was cared for by the Nipmuc, Massachusetts, Mohegan, Mohican, Narraganset, Nauset, Niantic ย Schaghticoke, Pocumtuc, Pequot and Wampanoag nations, and the affiliated tribes of the Wabanaki Confederacy.
At this time, New Englandโs Native peoples (sure, theyโre nonetheless right here!) establish as 16 distinct Nations and Tribes. They proceed to carry their floor, regardless of ongoing challenges to their sovereignty, akin to in 2020, when the US Division of Inside tried to revoke the belief standing of the Mashpee Wampanoag homelands.
The Final New England Highway Journey Itinerary
Youโll be driving so much, however this itinerary makes some extent of taking the scenic route, with frequent alternatives to cease in quaint small cities. Selecting which of them to characteristic is nearly like selecting between my youngsters, so in case you have additional time, keep an additional night time anyplace alongside the way in which!
With out additional ado letโs get began in your New England street journey!
Day 1: a Correct Day in Boston, Massachusets
- At this time youโll get essentially the most correct Boston expertise potential in a single day.
- Drive Time: None. Thankfully, Boston is certainly one of Americaโs โMost Walkableโ cities, as a result of itโs one of many worst locations to drive, a lot much less park.ย In addition to, it wouldnโt be a Correct Boston expertise with out taking mass transit, higher often called the โT.โย
Ahhh, Beantown. Welcome to Bahstan: a metropolis outlined by its wealthy historical past and sports activities tradition, stuffed with homey, Cheers-esque bars and a thriving theater scene, with harbor views round each nook and a bustling metropolis middle that someway feels each outdated and new on the similar time.
New Englandโs largest metropolis occupies the hilly peninsula often called Shawmut by its authentic stewards, the Massachusetts, Wampanoag and Nipmuc folks.ย
There is no such thing as a solution to see every part in Boston someday, however with some sensible planning, you possibly can see so much. My private desire โ extra of a bias โ is for the Italian North End and Charlestown, the place I ran a neighborhood program for a few years.
It doesn’t matter what time your flight will get in, you will get a full breakfast, and/or a cocktail, on the Friendly Toast within the Again Bay (name a Lyft or take the Orange Line Train to Again Bay Station).
A great way to see lots of sights in a brief period of time, particularly when youโre drained from a protracted flight, is to squeeze all of it in on a Duck Tour. The notorious Duck boat โ a World Struggle II-style amphibious car โ is a Boston icon in its personal proper! The 80-minute tour takes you previous landmarks like Boston Common, Faneuil Hall, and Quincy Market, earlier than plunging into the Charles River for a duckโs-eye view of town skyline.
For lunch โ or dinner, relying on when your flight will get in โ head to the outdated Italian North End. Locals argue to the demise about whether or not the pizza is best at Reginaโs or Umbertoโs, or if Modern Pastry or Mikeโs has higher cannolis. My favourite is whichever has the shortest line!
Comply with the Freedom Trail (marked by a redbrick line) by way of the charming cobblestone alleys of the North Finish and throughout the bridge to Charlestown. Take within the view from the Bunker Hill Monument (really on Breedโs Hill) earlier than hitting Paul Revereโs favourite hangout, The Warren Tavern, for dinner and/or drinks.
- Tip: Watch Ben Affleckโs The Town for an action-packed however surprisingly complicated introduction to Bostonโs oldest neighborhood โ plus a cameo by the proprietor of my favourite laundromat!
The place to Keep: The Harborside Inn gives one of the best worth for one of the best location, a brief stroll from the harbor, duck tour, Freedom Path, Quincy Market, and several other T stops. Or, when youโre feeling adventurous, you possibly can keep straight IN the harbor on a houseboat!ย (Be happy to pour a bit of tea over the aspect to essentially get within the spirit of issues, too.)
Day 1 Abstract

Day 2: Boston to Portland, Maine (with a spooky Salem stopover)
- At this time youโll head up the seacoast to Portland, Maine, stopping on the notorious city of Salem.
- Drive Time: 2-3 Hours
Earlier than hitting the street, seize breakfast and collect provisions on the Boston Public Market, an indoor market the place youโll discover every part from maple bacon glazed donuts to Kelp Smoothies.
Now itโs on to Salem, about 40 minutes north by way of the Essex Coastal Scenic Byway (Route 127) which takes you thru the elegant seaside communities of Swampscott and Marblehead. In contrast to Boston, Salem has ample public parking, and all sights are inside straightforward strolling distance.ย
If it werenโt for the 1672 Salem Witch Trials, Salem could be simply one other, albeit very beautiful, North Shore port city. As an alternative, this small city is the worldwide epicenter of all issues occult.
Within the twenty first century Salem, itโs nonetheless onerous to separate the historical past from the hype. My recommendation is to embrace the insanity, which in the course of the month of October is just about 24/7.
For a glance behind the hype, join Kenneth Gloverโs Morning Stroll Historical Tour. Kenneth offers an summary of the Witch Trails AND Salemโs Native American and maritime historical past as you stroll by way of Salemโs slim streets previous Seventeenth-century landmarks just like the Salem Witch House and Hamilton Hall.ย
After lunch on the Lobster Shanty โ well-known for its โheat beer, awful meals, surly waitresses, impolite bartenders, and cranky cooksโ โ immerse your self in witch kitsch earlier than hitting the street for the 1-2 hour drive to Portland. Get a psychic studying, refill on spell-casting provides, or go to the Salem Wax Museum.ย
If in case you have an additional day in Salem:ย
Leap again on Route 127 till your bladder provides you an excuse to cease in Manchester-by-the-sea, Gloucester, Rockport or charming Newburyport. (Facet notice from Lia: Newburyport is beautiful! I spent a cheerful summer time right here working at an internship on the harbor. Extremely advocate a pit cease!)
Say hey to New Hampshire for a scorching second (donโt fear, youโll be again) earlier than arriving in Portland, Maine, in what was as soon as the guts of the Wabanaki Confederacy. The drive from Salem to Portland is about an hour and forty minutes.
Portland, Maine, is the older, colder โ wiser? โ cousin of Portland, Oregon. Like their west coast counterparts, Portland Mainers are captivated with artwork, the outside, and their native microbrews, which youโll have the chance to pattern.
However first, cease in on the International Cryptozoology Museum, as a result of what higher solution to get into the temper for the Maine Woods than studying about massive furry cryptids? Notable exhibitions embrace Bigfoot hairs and Abominable Snowman scat. It’s also possible to decide up a Santa Yeti Christmas decoration for mother on the CryptoStore!
By now, you most likely want a drink, so itโs on to Allagash, Austin Street, and/or one other of Portlandโs native breweries for a palate-cleansing flight of beer or cider, earlier than chowing down on some nouveau, New England meals at Central Provisions.
The place to Keep: You most likely receivedโt be spending a lot time on the lodge, however the Inn at St John gives clear, quaint lodging at inexpensive charges. Or select one of many fancier West Finish B&Bs like Chadwickโs.
Day 2 Abstract

Day 3: Scenic Drive by way of Maine to Acadia
- Head down east alongside coastal Route 1 to Bar Harbor, stopping for lunch at McLoons Lobster Shack.
- Drive Time: 2.5-3 hours
Even when you ate breakfast at your B&B, you need to nonetheless cease at Tandem Coffee Roasters in your means out of city. You mayโt replenish the automobile at this transformed โ60s fuel station, however you possibly can refuel on single-origin espresso, cinnamon buns and yummy scones!
Maine has about 3,478 miles of coastline, greater than California (simply extra squiggly), and at the moment youโre going to see lots of it: waves crashing on rocky seashores, sailboat-studded bays, Hallmark villages and scenic lighthouses.
Take a detour down Route 130 to the Pemaquid Point Lighthouse, about 40 minutes round-trip, perched dramatically atop a layer cake of metamorphosed rock.
We promised lobster, and itโs time to money in within the state the place itโs essentially the most recent and most cheap! Cease for lunch at an genuine Maine lobster shack, just like the (deservedly) well-known McCloonโs Lobster Shackย in South Thomaston and Claws in Rockland, about an hour-and-a-half from Portland. These quirky roadside stands usually shut for the season across the finish of September โ verify the web sites for precise dates. However fall road-trippers are in luck: an exception is Hazelโs Takeout in Rockland, which stays open till November.
Whilst youโre in Rockland, take a look at the Archipelago, a retailer that helps artists and makers from Maineโs small coastal and island communities.ย
Proceed on Route 1 by way of historic downtown Camden. Cease simply up the street at Camden Hills State Park. Drive or stroll to the highest of Mount Battie for views of Camden Penobscot Bay and islands; views that impressed the poem โRenascence,โ by Edna St. Vincent Millay.ย
From right here itโs about an hour-and-forty-five minute drive to the gorgeous Acadia National Park, the jewel of Maine and arguably one of the best Nationwide Park on the Jap seaboard! Youโll be exploring tomorrow, so verify into your lodge and head to dinner.
For dinner, we advocate Side Street Cafe, a much less touristy spot by Bar Harbor requirements. It serves a wide range of all-American fare however itโs finest recognized for lobster rolls and blueberry pies, to not point out blueberry margaritas and blueberry ale.
The place to Keep: The closest city to the park is Bar Harbor. The charming Moseley Cottage Inn is the sweetest, most charming little quintessential New England B&B, and the Bar Harbor Inn & Spa is a extra upscale boutique lodge.
Resorts right here might be expensive, however there are some inexpensive, no-frills choices. Many guests to Acadia select to camp as a substitute. We all know itโs onerous to pack tenting gear in your suitcase, so we discovered one thing even higher โ glamping! Reserve a safari-style A-frame tent in Lamoine, about thirty minutes north of the park. This private bay retreat comes with a photo voltaic bathe, transportable camp bathroom and propane heater for cool fall nights.ย
ย Day 3 Abstract:ย
Day 4: Bar Harbor and Acadia Nationwide Park, Maine
- At this time youโll expertise certainly one of Americaโs most luxurious nationwide parks.
- Drive time: 0-3 hours, largely inside Acadia Nationwide Park
Route 1 was solely a scenic warm-up! To expertise Acadia National Park is to step again in geologic time โ mountains cut up by receding glaciers, waves crashing in echo chambers of volcanic rock, spruce-covered islets and infinite deciduous forest that bursts into colour every fall.
That is the sacred panorama of the Wabanaki folks, who nonetheless come right here to reap sweetgrass and go mountain climbing!
One of the best ways to understand Acadia is to hike the trails. If in case you have an additional day or two, it is a nice solution to spend them. Nonetheless, the park additionally has shorter trails that match into any itinerary, together with this one.
Head out early and seize breakfast (to-go or at certainly one of their picnic tables) from Hullโs Cove General Store. It’s also possible to decide up snacks and picnic provides; they’ve a full-service deli, baked items, pizza, and comfort retailer objects.ย
One choice is to depart your automobile on the Hulls Cove Visitorโs Center and take the Island Explorer shuttle bus, which picks up and drops off at well-liked locations throughout the park.
You may full the Beehive Loop, Ocean Path, or South Bubble Trail by lunchtime. Eat the picnic you packed from the final retailer, or head to the Jordan Pond House for popovers and tea.
After lunch, preserve mountain climbing, or tour park highlights. Trip the shuttle or take aย self-guided driving tour of the park (roughly three hours) culminating with mind-blowing views from Mount Cadillac. If potential, time your journey with the intention to watch the sunset from the summit.ย
For dinner head again to Bar Harbor for old school pub meals and brews on the Thirsty Whale Tavern, or, particularly when youโre staying in Lamoine, the Acadia Lobster and BBQ in Trenton.
Day 4 Abstract:ย
Day 5: Maine to New Hampshire, the Northeast Kingdom
- At this timeโs drive takes you west alongside the Androscoggin River by way of the city of Bethel and up into the gorgeous White Mountains of New Hampshire!
- Drive time: 4.5 hours
Begin with a hearty Great Maine Breakfast earlier than heading north and west to Bethel by way of Route 2, a couple of four-hour drive. Take a brief detour to see the Sunday River Covered Bridge in Newry. If the weathered truss bridge seems to be acquainted, thatโs as a result of it’s; the Sunday River Bridge is also called the โArtistโs Bridge,โ as a result of itโs mentioned to be essentially the most painted and photographed bridge on the earth.
Eat lunch and refill on snacks at Good Food Bethel, which is โ no kidding โ a espresso store, well being meals retailer, delicatessen, liquor retailer, AND BBQ joint in a single.
After lunch, take a look at the Maine Mineral & Gem Museum, house of the most important moon rock on earth.
Take the remainder of the afternoon to go raspberry choosing (when youโre there in July) or apple choosing (in September) at Gibsonโs Apple Orchard. The orchard retailer is open till round Thanksgiving, promoting home made cider, native honey and maple syrup, so itโs price a cease on a fall day!
From right here itโs solely a 30-minute drive to Gorham, New Hampshire, your base for exploring the White Mountains. Youโll discover the backbone of the Carter-Moriah range rising to the southwest.ย
As you cross over the New Hampshire border, youโll see a proliferation of billboards promoting issues like alcohol and cigarettes. New Hampshire is the โDwell Free or Dieโ state, and naturally demise is preferable to paying gross sales taxโฆ or sporting a helmet whereas using a bike.ย
For dinner in Gorham attempt The Notch Grille at The Glen House Hotel, the place the one factor higher than the meals is the views. Flooring to ceiling home windows face the Presidential Vary, evergreen slopes giving solution to granite escarpments blanketed with snow for a lot of the 12 months.
Within the Algonquin language, these mountains are often called Wobanadenock, โthe place of the excessive white or crystal/mica mountains.โ The tallest of those peaks, usually shrouded in clouds, is Mount Washington, house of a number of the highest wind speeds on earth โ thatโs the place youโre going tomorrow!
The place to Keep: Keep at The Glen House: If these firepits on the deck with sweeping mountain views donโt do it for you, maybe the complimentary breakfast and cookies will! Or lean into the log cabins/alpine chalet vibe and keep at this stunning vacation rental, with unimaginable views, a super-modern kitchen, and an enormous stone fire!
Day 5 Abstract:ย
Day 6: New Hampshire to Vermont (the White Mountains to the Inexperienced Mountains)
- At this time youโll climb Mount Washington and traverse the Kancamagus Scenic Byway in your solution to the Inexperienced Mountains of Vermont.
- Drive Time: 2.5 hours
Eat breakfast on the homey White Mountain Cafe and Bookstore, the place you too can decide up path maps and native curiosity books.
By now you will have seen the bumper stickers: โThis Automotive Climbed Mount Washington.โ Until you have got an entire day, and are a seasoned mountaineer, the easiest way to climb New Englandโs highest peak is by way of the auto street! (After which you possibly can decide up a bumper sticker, too!)
The slim, two-lane autoroad, accomplished in 1864, ascends 6,145 ft by way of a collection of steep switchbacks. There are NO guardrails. If that is an excessive amount of for you, no disgrace. Join the guided tour, and let another person do the driving.ย
The round-trip lasts about three hours, taking you from the leafy hardwood forest by way of boreal groves of evergreens and birch, gnarled conifers and blueberries, earlier than rising onto windswept alpine tundra. A lot of the 12 months, the summit is snowy, with thrilling views of close by peaks poking up by way of the clouds.ย
At 6,145 ft, Mount Washington could appear puny in comparison with peaks out west, however donโt be fooled โ as a result of its location on the intersection of storm tracks from the south and west, the summit experiences a number of the most excessive climate circumstances on earth. Winds as excessive as 230 mph have been recorded on the Mount Washington Observatory. You might be reassured that the auto street will likely be closed if circumstances even remotely strategy that.
If you wish to forgo being in a automobile altogether, you possibly can take the long-lastingย Mount Washington Cog Railway to the highest,ย which was the primary mountain-climbing cog railway ever constructed. Opening in 1868, the biodiesel and steam train takes about three hours round-trip. On the summit, you possibly can pick a memento on theย Sherman Adams Summit Buildingย and go to theย Tip Top House, a former lodge relationship again to the nineteenth century that was became a historic website. Itโs price noting that from Oct. 18 to 31, thereโs aย special trainย that takes you to the north and east of the mountain.ย
After your mountain tour, take pleasure in some stylish consolation meals on the four-season porch on the Wildcat Inn and Tavern in Jackson. After lunch, itโs time to hit โKanc,โ or Kancamagus Scenic Byway, which cuts by way of the guts of the White Mountain Nationwide Forest. Itโs solely about an hour and forty-minute drive from Jackson to Littleton, however go away extra time, as a result of thereโll be numerous alternatives to cease and ooh and ahh over the foliage, take a brief hike, or verify some extra covered bridges off your listing.ย
Final cease in New Hampshire is Littleton, an enthralling mill city that always flies underneath the vacationer radar. Seize a beverage or snack on the Inkwell Coffee & Tea House or just stretch your legs alongside the half-mile Riverwalk.ย
- Psst: A number of of those stops โ and an entire bunch extra โ are coated in our guide to fall in New Hampshire! New Hampshire is sufficiently small to base your self in a single spot and take scenic drives to see the remainder of the state, so when you really feel like spending a couple of additional days within the White Mountains, head over to that publish for extra journey suggestions.
Itโs time to depart gorgeous New Hampshire and dive into charming, stunning Vermont. From Littleton, observe Route 2 east to the โNEKโ โ North East Kingdom of Vermont โ land of mountains, lakes, small farms, and ICE CREAM.
Thatโs proper: you possibly canโt go to Vermont with out making a pilgrimage to the ice-cream shrine of Ben & Jerryโs in Waterbury (about an hour and a half drive from Littleton). Take a Factory Tour and go to the Scoop Store, serving classics like โCherry Garcia,โ in addition to blasphemous new โNetflix Unique Flavorsโ like โNetflix and Chilled.โย
Drive twenty minutes north to the village of Stowe, the place youโll be staying tonight! This ski resort vacation spot hangs onto its small-town appeal, with a energetic major road anchored by an iconic steepled church and native companies like Laughing Moon Chocolates and Shawโs General Store.
For dinner, head to Stoweโs hippest pizza place, The Deep End, the place you order a drink from the refurbished airstream bar!
The place to Keep: E-book a room on the Timberholm Inn, a comfortable mattress and breakfast overlooking the mountains.
Day 5 Abstract:ย
Day 7: The Two Faces of the Berkshires
- At this time, youโll take the again roads to the Berkshires by way of the Inexperienced Mountain Nationwide Forest, stopping at MASS MoCa in North Adams, Massachusetts.
- Drive Time: 3.5 hours
Begin with breakfast at The Skinny Pancake, a Vermont chain thatโs really higher recognized for its candy and savory crepes that includes elements like maple pulled pork, native cranberry compote, and hazelnut unfold.ย
From Stowe, take Route 7 south. Youโll keep on 7 for the following three hours. For a lot of the means, 7 is a rural, two-lane freeway, winding by way of quintessential Vermont countryside: purple barns, dairy cattle, and rolling inexperienced mountains. You already know, typical jaw-dropping New England surroundings.
Arriving in North Adams, simply over the Massachusetts border, youโll see one other aspect of New England: a former industrial city thatโs reinventing itself as an arts middle.ย
Eat lunch at Lickety Split, a family-run eatery and ice cream parlor on the Massachusetts Museum of Contemporary Art (MASS MoCA). The menu is straightforward โ soups, salads, quiches and sandwiches โ however made out of the freshest locally-sourced elements. The ice cream can be made in-house, utilizing flavoring methods pioneered by Ben & Jerryโs rival Steve Herrell.
The museum has reworked an deserted brick manufacturing unit complicated right into a multi-media artwork house. The football-field-sized Constructing 5 homes epic installations, like Glen Kainoโs โWithin the Gentle of Shadows,โ by which hundreds of suspended metallic shards venture otherworldly patterns of sunshine throughout the huge warehouse house.
Now itโs on to the Berkshires. Simply an hourโs drive south lies the playground of wealthy Manhattanites. You may hardly blame them: southwestern Massachusetts is each culturally wealthy and classically scenic.
Nowhere is that this higher epitomized than at The Mount, the sprawling romantic property of writer Edith Wharton. Home excursions finish at 5pm, however the grounds of the 1902 mansion are open free from daybreak till nightfall.
Wander freely across the intensive gardens designed by Wharton herself, impressed by her travels to France and Italy. For those whoโre left wanting extra, return after dinner for a ghost tour of the property, which has been featured in a number of episodes of Ghost Hunters.
Keep on the historic Church Street Inn in downtown Lennox, steps from fashionable eating places like Alta, a Mediterranean-style cafe and wine bar, the place you possibly can dine alfresco and watch the attractive folks โ and drained vacationers โ move.ย
Day 7 Abstract:ย
Day 8: Connecticut, Rhode Island, & Cape Cod
- ย At this time youโll move by way of three totally different states in your solution to Cape Cod, stopping for lunch and surroundings on the Connecticut coast and Newport, Rhode Island.ย
- Drive Time: 5.5 hourย
Eat breakfast on the porch at Opheliaโs, the Church Street Innโs personal restaurant, the place the menu ranges from huevos rancheros to lemon ricotta pancakes with blueberry compote and โ after all โ native maple syrup. (For those who will need to have Aunt Jemimahโs, cover it in your purse).
At this time youโll be protecting lots of floor, however itโs stunning floor. Ignore all these indicators for the Mass Pike and keep on Route 7 by way of Stockbridge and Nice Barrington. Youโll keep on Route 7 for the following hour, earlier than chopping by way of Litchfield Hill to Torrington.
From there, itโs about one other hour and forty-five minutes to the coast. No, this isnโt essentially the most direct route, however belief me, itโs a lot prettier than the 91 hall and nicely definitely worth the detour.
For those whoโre a Julia Roberts fan, cease for lunch at Mystic Pizza, which is an actual place with first rate pizza and plenty of film merch. Or, go for Kamp Dog in New London, โNew Englandโs Best Wienery.โย
Now that you justโve dined in type, youโre able to enter Newport excessive society. Set your individual tempo on this 1-2 hour Self-guided Driving Tour, which takes you previous the โsummer time cottagesโ โ AKA gilded age mansions โ of the wealthy and well-known.
From right here, itโs a bit of over an hour (if the visitors Gods are smiling) to your penultimate vacation spot: Cape Cod!
For the following two nights, lease a beach cottage in East Sandwich, full sweeping ocean views, hammocks, and your very personal personal seaside entry. Take a sundown stroll alongside the white sand seaside earlier than having fun with dockside boat-to-table delicacies at Fishermanโs View.ย
Day 8 Abstract:ย
Day 9: Cape Cod Magic
- ย Relaxation and play on the decrease Cape.
- Drive Time: 0-1 hour
Youโve been on the street for over every week. Youโve earned a relaxation, and what higher place for it than Cape Cod, the flexed arm of Massachusetts.ย
Sandwich could also be simply over the bridge from the โmainland,โ however itโs quintessentially Cape Cod, with its sandy seashores, salt marshes, lighthouses, and cottages with weathered gray shingles.
Sandwich is Cape Codโs oldest English settlement relationship again to 1639, and the land adjoining stays sovereign to the Mashpee Wampanoag, the primary folks to come across the Pilgrims.
Sleep in as late as you need, then seize breakfast at Cafe Riverview, a preferred spot staffed by college students from the native highschool.
After breakfast, spend the morning hanging out out on the seaside. Sandwich is positioned on the Bay aspect of Cape Cod, so the waves are calm. The seashores are sheltered by sand dunes coated in lengthy waving grasses, which fade to pale straw in autumn.ย
Stroll the Sandwich Boardwalk whilst you can. The 100+ 12 months plank bridge, which extends 1300 ft throughout the salt marsh to Cape Cod Bay, is ready to be demolished soon and changed with one thing uglier and extra structurally sound.ย
Eat lunch at Cafe Chew, โSandwichโs Sandwichery.โ I donโt know what the Earl of Sandwich (alleged inventor of the sandwich) would make of their โOatsy-Groatsyโ sandwich with cucumber, child spinach, tomato, feta cheese, pureed purple pepper, caramelized onion, and hummus in an entire wheat wrap, however it sounds good to me.ย
Stroll the Sandwich Historic District for a final glimpse of the sixteenth century earlier than returning to modernity. Tour the interiors of Cape Codโs oldest houses, the Hoxie House and the Wing Fort House. They’re at present closed as a result of pandemic, however you possibly can nonetheless recognize the post-medieval timber body building, with uneven โsaltboxโ formed roofs from the surface.ย
The irresistibly photogenic Dexter Grist Mill, inbuilt 1654, overlooks Decrease Shawme Pond, which is shaded by weeping willow timber and residential to households of geese and swans. The mill nonetheless operates, and from Could by way of September you should buy a bag of its fresh-ground cornmeal.ย
Eventually, itโs time to strap in your bib for a closing feast of fried seafood and butter-drenched lobster at Mattakeese Wharf.
Day 9 Abstract:

Day 10: Returning House
- Full the circle (blob?) again to Boston. If in case you have time, cease by within the well-known city of Plymouth. Drop off your rental automobile and catch your flight house!
- Drive Time: 1.5-2 hours
Although itโs your final day, it doesnโt imply that you mayโt squeeze a bit extra New England historical past in (in case your flight time permits, that’s!).
Earlier than you permit Cape Cod, eat a traditional Ameican breakfast at 6a Cafe then hop on the street in the direction of Plymouth.
Plymouth, Massachusetts, after all, is the place the Mayflower Pilgrims landed in 1620 and the โnew worldโ was born (at the least to British of usโAmerica was already inhabited). For good or in poor health, Plymouth was the primary colony established by the pilgrims, and it holds one of many high spots in American lore.
A pure first cease is the Plymouth Rock, which can or might not be the โactual rockโ, however was recognized because the spot of the Mayflower touchdown in 1741,ย 121 years after the very fact.
Whilst youโre within the space, you possibly can take a look at the duplicate ship the โMayflower IIโ, in addition to Historic Patuxet, the place Native Peoples lived for 12,000 years earlier than being entirely wiped out by an epidemic. It’s also possible to go to the Plymouth Colony, to see how the Pilgrims labored and lived. Your entire museum complicated is immersive with actors in interval costumes, and you could possibly simply spend the entire day studying in regards to the individuals who as soon as lived within the space.
- Facet Be aware: On the Plymouth Colony youโll get an opportunity to satisfy Liaโs problematic ancestor, Miles Standish. Captain Miles Standish was first mate of the Mayflower and the navy chief of the Pilgrams, and was additionally the one individual on the Mayflower to be overtly non-religious โ he by no means joined the church. Why is he problematic, you ask? Nicely, as navy chief of the Pilgrims, he kind of unintentionally ended the peace between the Pilgrims and the Indigenous peoples by violently attacking them with out simply trigger, which freaked everybody out and, I feel, probably began the ball rolling down a path that will finally result in the virtually full genocide of the Native Individuals. So. Huge yikes.
For a chew for lunch earlier than you head to the airport, take a look at Dillionโs Local in Plymouth. You mayโt go unsuitable with their fish & chips or Cap Cod Ruben!
After which, itโs time to move again to Boston to catch your flight. Boston is 45 minutes to an hour away from Plymouth, however be sure to depart loads of time earlier than your flight as a result of visitors is unpredictable!
What to Pack for a New England Highway Journey
One factor folks both adore or despise about New England is that we’ve very distinct seasons. Youโll must pack accordingly!
- Layers: Within the fall, the evenings and mornings can get very chilly, whereas daytime might be fairly snug. Pack lengthy and quick sleeves, and skinny sweaters that may match simply underneath a fleece jacket or wool coat; thatโs until youโre from Arizona, or planning to hike Mount Washington, then you may also need certainly one of these packable down jackets. And you should definitely pack a couple of cute hats, scarves, and gloves for maximium fall cuteness and coziness! In the summertime, you most likely receivedโt want greater than a hoodie at night time, however deliver a fleece jacket and windbreaker for the mountains.ย
- Bathing suit: Youโll be getting some good seaside time on this street journey! However contemplate a wetsuit when youโre planning on spending any severe time within the ocean. Even in summer time, common water temperatures stay within the 60s.
- Tevas or sneakers: Youโll need close-toed sneakers for strolling alongside rocky seashores.
- Umbrella and rain jacket: Weโre susceptible to 1-3 day stretches of wet climate any time, and scorching summer time days can produce explosive pop up thunderstorms.
- Mosquito and tick repellent: Essentially the most harmful animal in New England will not be the moose, and even the nice white shark, however the mighty deer tick. Because of the deer tick, which isn’t any bigger than a sesame seed, New England hasย the nationโs highest price of lyme illness. Pack a pair of pointy tweezers for safely eradicating a tick as soon as it has embedded in your skin. But when it makes you’re feeling higher, Iโve lived in New England most of my life and Iโve by no means as soon as had to do that.
- Mountain climbing gear: You donโt must go loopy at LL Bean, however youโll need trail sneakers or hiking boots; long, lightweight pants (due to the ticks), and a small day pack for water, snacks, and many others.ย
10-Day New England Highway Journey Map
Weโve created a map of this New England street journey! It consists of the itinerary highlights (i.e. the place you may be driving to and staying) in addition to the final driving instructions (which embrace different places simply so Google will take you the proper route). Reserve it for offline use in case your web or GPS cuts out. And you should definitely bookmark this web page to refer again to whilst youโre planning!
About Our Contributor: Anna Laird Barto is a contract author who has lived in every single place from Cuba to Wisconsin however is now based mostly within the wild west of Massachusetts. Her writing has appeared in a wide range of journey, well being, and literary magazines together withย Fodorโs, Hobartย andย Wanderlust. She helps her writing behavior by working at a non-profit household middle. To learn extra of her work go toย annalairdbarto.com.
Are you able to hit the street? Which cease on this New England street journey itinerary are you most enthusiastic about? Tell us within the feedback under
Psst: Planning some East Coast getaways? Check out a few of our different posts!

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Our High Journey Ideas & Assets
- Reserving Flights: To attain flight offers, search on Skyscanner or Kayak. Cash-saving suggestions: fly mid-week or on the weekend; fly carry-on solely on a funds airline; and take red-eyes or early morning flights.
- Lodging: We normally keep in budget-friendly, trip leases, boutique accommodations or personal rooms in hostels. We use Booking.com to ebook accommodations (we love their versatile cancellation coverage) and Hostelworld to ebook hostels (low deposit, straightforward change/cancellation, and wonderful opinions). For trip leases, we desire to ebook utilizing VRBO (they have decrease charges and higher help than Airbnb, and we’re not followers of Airbnb’s unethical monitor document.) It’s also possible to ebook trip leases on Expedia and Hotels.com. We have additionally used TrustedHousesitters as each hosts (for our house and our fur-child) and vacationers!
- Journey Insurance coverage: We all the time, all the time, ALWAYS purchase journey insurance coverage for worldwide journeys, and we STRONGLY counsel it – go to our Travel Insurance Guide to seek out out why. We advocate both World Nomads or SafetyWing for worldwide journey insurance coverage. SafetyWing is among the few insurance policies that covers Covid-19, they usually have wonderful month-to-month insurance policies which can be good for Digital Nomads and long run vacationers!
- Vaccines & Meds: We use the journey guides on the CDC website to analysis beneficial drugs and vaccines for worldwide journeys. We all the time advocate getting each vaccine beneficial by the CDC! You will get them at your major care physician’s workplace or a walk-in pharmacy.
- Excursions: We love reserving guided excursions, particularly meals excursions and strolling excursions, to get an area’s perspective and a historical past lesson whereas sight-seeing! We ebook our excursions utilizing Viator and GetYourGuide.
- Transportation: We use Rome2Rio to determine the way to get from place to put utilizing public transit, and ebook native transportation on-line utilizing Bookaway wherever we are able to. Once we ebook a rental automobile, we use Kayak to match rental firms and discover one of the best deal.
- Baggage Storage: Each time we’re testing early or benefiting from a protracted layover, we use Stasher or LuggageHero to soundly retailer our baggage whereas we’re operating round. On Stasher, you should use the code PW10 for 10% off!
- What to Pack: Here are the travel essentials that we deliver on each journey. We even have packing lists for hot weather, cold weather, and plenty of extra. Check out all of our packing guides!
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