New England Fall Road Trip Tips

Road trip through the New England states and take in fall in all its glory.

Clearly I’m partial but, when the weather cools, there’s no better place to experience autumnal glory than throughout the cloistered states of New England. From Vermont, where your breath will surely catch at the sight of rolling mountains transformed by trees ablaze, to Maine, where lobster boats shimmer against the rocky shoreline and choppy waters. Now is the time to hop in your car and go north.

A few weekends ago I did just that, packing up a few sweaters, and some jeans and boots in preparation for the cooler temps, and tossing my atlas in the back seat (pro tip: if you’re driving to New England, get an IRL map. You’ll need it once your cell phone reception inevitably cuts out). Those mountains, back roads and byways will always feel most like home to me, and I’m always over enthusiastic excited to share my recommendations when I hear a friend (or perfect stranger) is headed in the direction of where I’m from. Today I’m sharing those recommendations with you, whether you’re headed for up for a proper road trip or just visiting one locale. Follow along state by state below, and be sure to add your own recommendations in the comments.




Begin your journey by flying — or driving — into Albany, NY. True, it’s technically not New England, but a quick drive will bring you to the shop-lined streets of Troy, a town absolutely worthy of at least a few hours of browsing and brunching. Once satisfied, bid adieu to the state of New York and hop on NY-7e to bring you across the border to the great Green Mountains of Vermont. Follow US-7E, being sure to stop off in Bennington to visit Bennington Potters. From there, ignore the pleas likely emanating from your GPS and eschew US-7e for US-7A, which will bring you along a more scenic drive and straight through the heart of downtown Manchester, VT, former home of Robert Todd Lincoln, the only child of Abraham and Mary Todd Lincoln to survive to adulthood, and Jake Burton, founder of Burton snowboards and snowboarding as we know it.

Manchester’s historic district yields an abundance of bed and breakfasts to choose from (and is there anything more Vermont than a bed and breakfast?), but one of the many Air BNBs in the area would be my choice to get a local’s perspective. History buffs might consider stopping off at Hildene, the historic Lincoln family home, located along route 7A. Personally, I recommend grabbing breakfast at Up for Breakfast and a quick browse around Northshire Books (though, in this incredible independent bookstore hours seem to pass in merely a blink). After breakfast, head over to the Southern Vermont Studio Art Center to walk through the sculpture field, before taking a drive to Equinox Mountain, the tallest peak in the Taconic Range. Equinox offers a number of activities, depending on what you feel up for. Choose from hiking trails and picnic vistas or take a drive along Skyline Drive, a 5.2 mile journey to the summit that offers overlooks and plenty of picnic areas from which to enjoy a packed lunch. Close out your day in Vermont with a spectacular dinner at Brasserie L’Oustau (quite fancy) or go low-key with a stop at Cilantro Taco.

After exploring this historic Vermont town, you can choose to drive 2.5 hours north along route 22A to check out Burlington, VT (always worth a visit), or take my route and point your compass in the direction of the Granite State. State route 11 will take you through the Green Mountain National Forest and through the towns of Londonderry and Chester. Hop on 91 North and link up with route 4/104 to cross the border to New Hampshire…




New Hampshire

Once over the border of New Hampshire, take route 104 to route 25, where you’ll pass through the village of Meredith along Lake Winnipesaukee. Follow 25 to route 113 and you’ll find the small but lovely town of Tamworth, home to the Tamworth Lyceum, Tamworth Distilling (you thought I could talk about New Hampshire and not mention the Distillery?), and the Barnstormers Theatre. After a tour of the distillery (be sure to call ahead), head over to the Lyceum for a coffee or something stronger and join in on one of the many demonstrations or live shows that happen nightly (see all events here). Ask a local for directions to the fire tower trail, located close by, for a quick hike that culminates with an excellent view of the White Mountains.



After departing Tamworth, hop on Rt. 16 North and make your ways towards North Conway. Along the way you’ll pass by Chocorua Lake, which offers a stunning view of it’s namesake mountain (a challenging hike that offers epic views when completed) and a little while later, the entrance to Rt. 112, better known as the Kancamagus Highway (or “the Kanc” if you’re local). If time and weather allows, take a left on this mountain road, which winds through the expansive White Mountain National Forest, depositing you in Lincoln, NH on the other side. But it’s the journey here, not the destination, that matters. Along with generous hiking and swimming opportunities (expect to rough it, no manicured swimming holes here), the Kanc is a winding mountain road with gorgeous views. Drive slow, both to take it all in and to carefully traverse the difficult hairpin turns that populate the road.

After a day on the road, stop off in North Conway, where you’ll find plenty to choose from for a bite to eat. Make like a local and grab a beer at Moat Mountain Smokehouse before heading over to Flatbread for a wood-fired pizza. In the AM, grab a maple latte (made with real maple syrup of course) and a bagel or smoothie from Frontside Coffee Roasters before going on your way.

NE Small

In the White Mountains, the great outdoors are the thing. There’s plenty of shopping, yes, but it’s the plentiful trails, rivers, lakes and scenic drives that make this place special. Keep your eyes wide and you’ll see trail markers lining the side of nearly every road and highway. A trip up Mount Washington, the tallest peak in the Northeast, on foot or by car is always a good idea (I recommend avoiding the Cog Railroad at all costs).

After a day or two in New Hampshire, it’s time to move on…hop on Rt. 153 to pass through the scenic town of Eaton, before making your way across the border to Maine…





Leaving New Hampshire behind, find your way to Rt. 113 s to Rt. 25, which will bring you in the direction of my most-loved city, Portland, ME. Get on the road early and head to the waterfront and straight to Becky’s Diner for a good old fashioned diner breakfast, grabbing a tide chart on the way (also available online). Becky’s is kind of legendary and a favorite among locals, so while you might have to wait a bit, I can almost guarantee you’ll meet someone interesting (the last time I was here I met someone who went to high school with my mother). The fare here is basic diner grub, though feel free to get fancy with the lobster & swiss omelet. Once you’re fueled up, pack up a picnic lunch and hop over to Casco Bay Lines and take one of the many ferries out on Casco Bay. You have several options when it comes to the ferries, either hopping off at one of the islands (I recommend Peaks or Long) or simply taking the mail boat out for a tour. Either option pays off with incredible views of fall foliage and the Maine coast, and possibly even a bald eagle or two.



After returning from sea, jump on Rt. 1 and head over to Scarborough, ME. If you’re feeling cultural, stop off at the Winslow Homer Studio (purchase tickets ahead of time). A major location in the history of American art, this pretty seaside studio is where Homer painted the majority of his works. Located on Prouts Neck, be sure to walk the coastal path that skirts the edge of the rocky shoreline just outside the studio’s doors.


If you’re not tempted to stop at one of the many seafood shacks that dot the roadside, or are looking for something slightly chicer, close out the day at Earth at Hidden Pond in Kennebunkport, an award winning locale that offers a “farm to fork” menu. Or drive further south and back into New Hampshire for a locally-sourced, but down to earth meal (and a milkshake, because why not?) at The Friendly Toast in pretty, historic Portsmouth, NH, which offers plenty to look at, either out the front picture windows or on the walls, which are decked out in ephemeral kitsch from the ’50s and ’60s.

In the morning, rise bright and early and head in the direction of I-95 S. It’s time for the next state…




Take 95 to route 62 and head in the direction of the North Shore town of Beverly, MA. Located just 30 minutes north of Boston, this coastal city that feels more like a town sits next to Salem and just below Rockport and Newburyport (both worth exploring, but the way). Grab a latte and breakfast at Atomic Cafe on Cabot St. and tote your food down to the shoreline to watch the boats and seagulls while you plan out your day.

Boston’s North Shore is comprised of numerous small towns and cities, all with their own distinct personalities and characteristics, and all worth exploring. With one of these locales as a home base for a few days, you can easily see them all using the commuter rail, which will also bring you straight to Boston in 40 minutes or less. Personally, I recommend Salem.

After downing a coffee or two, walk, drive, or take the train from Beverly over to Salem, only a couple miles away. There’s plenty to do in “Witch City,” especially during the months of October and November, when Salem shows its true colors and embraces its storied, and rather dark history. Pass by the slightly corny Halloween-themed attractions in favor of the more authentic House of Seven Gables, which inspired author Nathaniel Hawthorne’s book of the same name. If you’re not exhausted on museums after touring the mysterious house, pop over to the superb Peabody Essex Museum and wander through the galleries and Yin Yu Tang house, a full-size, fully-reconstructed Chinese house from the Qing Dynasty (1644-1911). Before grabbing lunch or dinner (Passage to India is perfect for either) pop into Haus Witch for gorgeous housewares and Modern Millie Vintage & Consignment for unique clothes and accessories from all eras. Close out the evening with open mic night at Gulu Gulu Cafe or grab nightcap at Moroccan-inspired Opus.

From Salem, Boston Logan International Airport offers a convenient way to return to life as usual and is just a short train ride away. Though, before leaving the gorgeous foliage behind, I recommend taking an afternoon to explore this historic city. Boston in autumn is quintessentially New England collegiate and alive with the beauty of fall.



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  1. Beautiful post. I went to college in Upstate New York as well as in Vermont for graduate school so I can really relate to this post. Have never made it to Maine or much of Massachusetts though. Lovely photos and great recommendations.

  2. My love for mountains and fog always drives me west, but the east has an incredible charm that just can’t be found anywhere else. All these photos are so beautiful- would definitely love to check this part of the country out, especially in the fall!

  3. We have been in Fl. 27 years BUT – I grew up in Pa., married & to Ma. then had a summer place on “Thomas Pond” S. Casco, Me. for 30 years SOOOOOO this article brings back sooooo many “Memories” YES, this area (NEW ENGLAND) is BEAUTIFUL & has the SEASONS to prove it !! Used to take the “kiddos” on the Kangamangus trail, in N.H. every summer, to wade in the (ice-cold) water then hit all the “shops” on the way back to Maine. Wish ALL could visit there, one day !! PJsMusic

  4. In my last order of “remarks” I forgot to mention more about N.H. Ever hear of “THE OLD MAN OF THE MOUNTAIN” (on a 25c coin, too ??) Well, that was quite the”natural”attraction of a mans head on the side of the mountain BUT several years ago it “discentigrated” What a shame !! Summers we would take “company” to see that & the “COG RAILWAY” !! That, too is quite the experience, of a visit to the gift shop then, ride to the top of Mt. Washington. Today, I check the weather to see how many days it is the COLDEST, there. From our place, in Maine we’d watch for the 1st snow fall, there, also !! M.J.M.

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