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Published: 2/22/2023
Plan Your Next New England Fall Trip For Late Autumn
The concept of a New England fall trip isn’t exactly novel. As home to the country’s most celebrated fall foliage, Americans are pretty keen to see New England in autumn. But did you know there’s an enchanted moment each year when you can enjoy the best New England fall activities without crowds?
I’m dead serious.
All you have to do is wait for the leaves to fall.
After spending an all too short week in the northeastern United States last autumn, I can assure you New England is absolutely worth exploring after peak fall colors. Over the course of seven days, we used planes, trains, and automobiles to explore Portland, ME, New Hampshire’s White Mountains, and the Connecticut River Valley in Vermont. We found peak fall colors in Boston where we started and ended this New England fall “road” trip.
There’s a certain magic to be found in New England between the leaves falling and the snow flying. I hope this post convinces you to go find it. Read on for our full 7-day New England fall trip itinerary.
Why Visit New England in Late Autumn/Stick Season
I know what you’re thinking. “Ada, if I’m going to New England in the fall, I want to see amazing fall colors!”
No question about it; the fleeting fall foliage season in New England offers unparalleled beauty. But New England falls aren’t all sunshine and gorgeous vistas. If you visit during the approximately two weeks of peak color, expect congested roadways, overrun hiking trails, and inflated prices.
I “strategically” planned this trip for “stick season.” (In truth, the last week of October is my first opportunity to leave my seasonal business.) Colors peak in New Hampshire’s White Mountains in mid-October, often right around the Indigenous Peoples’ Day federal holiday. In the weeks leading up to our trip, I watched in horror as Instagrammers documented traffic backed up to the freeway as people waited for parking spots at popular trailheads I planned to visit.
But the first stiff winter wind blows away both the visitors and the leaves. When we arrived in late October, quiet roads and empty hiking trails greeted us. We felt so lucky to explore New England’s unparalleled beauty on our own terms.
What is “stick season” in New England and why should I see it?
Stick season might not sound super appealing. Maybe the term “barren” come to mind? As a northerner, it’s truly one of my favorite times of year. Basically, it’s that brief window between leaves falling and snow accumulating. It’s also the least crowded time to visit New England.
With the passing of another tourist season, you might pick up a sense of euphoric relief among local business owners. That is if you can find any. Expect a fair number of businesses to be catching their breath with a seasonal hiatus. If you’re traveling outside of large cities on your New England trip, definitely plan to prepare your own meals this time of year.
Although vistas won’t be as picture-perfect as they were just a couple short weeks before, stick season in New England gives you unobscured views of winter . . . without having to wade through snow. I find the crisp air this time of year makes for excellent hiking. Just use a little extra caution on the trails; all those fallen leaves can get slippery underfoot!
Our New England Fall Trip Map
If you’re headed to New England in fall, flying into Boston is your cheapest option. Although I’d already been to Boston and the purpose of the trip was to visit New Hampshire, Maine, and Vermont, (my 47th, 48th, and 49th states respectively!) it was a no-brainer to save a couple hundred bucks per plane ticket and fly into Boston rather than Portland, ME. It’s just a 2.5 train ride from Boston to Portland.
We took Amtrak up to Portland and rented our car there. This worked pretty well and saved us from Portland’s notoriously hefty parking charges. However this “trains, planes, and automobiles” approach to New England travel created a lot of transfers – definitely the most wearisome part of the trip. We leaned into taxis, ride shares, and a couple “longer than we wanted” walks with our suitcases to get to our exact destinations.
Our Day by Day 7-Day New England Fall Trip Itinerary
Day One: Arrive Boston
By the time our slightly delayed plane landed at Boston’s Logan International Airport, night had fallen. We checked in at our downtown hotel and immediately set out in search of dinner.
Eat: We headed straight to Legal Crossing, the Legal Sea Foods restaurant in Downtown Crossing. My mom and I had fond memories of this restaurant from our 2018 visit. We wanted Dad to sample their clam chowder too. Although we didn’t have a reservation, strategic stalling near the hostess booth eventually landed us a table. The clam chowder lived up to our hype and we enjoyed another Legal Sea Foods favorite: bang bang cauliflower.
Drink: After dinner, we settled in for a nightcap at the Last Hurrah bar in the Omni Parker House Hotel. A martini and some Boston Cream Pie was the perfect close to out long travel day. Our street view table provided excellent people watching!
Stay: The Omni Parker House Hotel is not only the oldest hotel in Boston, it’s one of the oldest continuously operating hotels in America. Learn more in my post about one of the hotel’s most famous ghosts!
Day Two: Taking the Downeaster Train from Boston to Portland, ME
We spent the morning in downtown Boston, then grabbed the Amtrak Downeaster to Portland. Despite missing autumn foliage in New Hampshire and Vermont, our train took us straight through eastern Massachusetts’ peak colors. Beautiful!
Eat: Portland’s known for its local food scene, so we made the most of our short stay with an excellent dinner at Street and Co. You’ll find this seafood offshoot of the famed Portland eatery, Fore Street, tucked down a cobblestone alley. It was the perfect place to enjoy my first-ever whole lobster!
Drink: Even if you prefer stiffer drinks, try the Italian Ice mocktail at Street and Co.
Waypoints: While in Boston, we picked up the Freedom Trail in Boston Commons and walked as far north as Old North Church. We did a walk-about in eastern Portland too, including Portland Observatory (closed for season) and the Eastern Promenade. The Eastern Promenade includes parks, memorials, a War of 1812 graveyard, and fabulous views of Portland Harbor and its many islands. Honestly, there are so many fun things to do in Portland – I wished we’d had more time to explore!
Stay: After sharing a petite double room in Boston the night before, we spread out in a two-bedroom suite at the Residence Inn by Marriott Portland Downtown Waterfront.
Day Three: Explore New Hampshire’s White Mountains via the Kancamagus Highway
After a relaxed morning in Portland, we picked up a rental car at the Portland International Jetport and hit the open road! We had no timeline for the day, other than eventually arriving at our vacation rental in Franconia, New Hampshire. I want to see as much of New Hampshire’s natural beauty on our 2.5 hour drive; I think we succeeded.
Eat: Before leaving Portland, I swung by The Holy Donut for an assortment of Maine potato donuts. We randomly stopped at Brownfield Country Market, which appears to be a sort of family-owned ALDI – to stock up on incredibly cheap groceries for the next couple days.
Waypoints: Other than a grocery run, we drove straight through Maine. We made our first “official” stop at the Saco Ranger Station outside Conway, NH. A super helpful ranger hooked us up with a map and guide to the Kancamagus Highway. We spent about 3 hours on the 34-mile national scenic byway (full guide coming soon!) then veered north through beautiful Franconia Notch.
Our rental house abutted Fox Hill Park, a 99-acre forest park owned by the town of Franconia. We briefly stretched our legs on the park’s trails (and meet our very friendly next-door neighbor and his pup) before settling in for the night.
Stay: Franconia Vacation Rental – House on Gale River. With river frontage on one side and a town park behind, this was the perfect little house for us.
Day Four: Vermont and King Arthur Baking Company
Back in July when I started dreaming up this trip, I booked a four-hour afternoon class on Savory French Tarts at King Arthur Baking Company outside Norwich, VT. I’d hoped to start our morning off with breakfast at Polly’s Pancake Parlor before making the hour drive down to the Norwich, VT/Hanover, NH area. Polly’s was taking a well-deserved seasonal break, so we just had a beautiful drive, including stunning Sugar Hill Road right outside of Franconia.
Eat: When I signed all three of us up for the tart class, I didn’t quite realize that we’d be driving home with a total of six full sized savory French tarts: three spinach quiches and three French onion galettes. Needless to say, King Arthur Baking Company fed us for several dinners. We even left two tarts (with permission) for the housekeeping staff in our vacation rental!
Waypoints: Before leaving for Vermont, we did a self-guided tour of Franconia Art Walk. This short walk took us past several art installations, through downtown Franconia, and along the Gale River. Before our class, we stopped at Dartmouth College, located right across the Connecticut River from King Arthur Baking Company’s headquarters. Pro tip: don’t accidentally visit on homecoming weekend!
We arrived at the beautiful King Arthur Baking Company campus with plenty of time to eat lunch in their courtyard and do a little shopping before checking into our classroom. If you enjoy baking and find yourself in Vermont, I definitely recommend taking a King Arthur Baking Company class. We loved the classroom camaraderie and our pate brisee skills are on point now!
Stay: Franconia Vacation Rental – House on Gale River
Day Five: Franconia to Boston
All too soon, we said good-bye to our sweet little spot in Franconia. While we didn’t intend to spend the entire day in transit, a two-hour delay on our 2.5 hour train ride back to Boston got us into the city after dark. We felt lucky that, unlike almost all of our train mates, we didn’t have tickets to the Boston Celtics game!
Waypoints: Before we officially hit the open road for the day, we hiked Artist’s Bluff Trail, just east of Franconia. This short, but surprisingly challenging, one-mile hike is a very popular New England fall activity. I knew just two weeks before our visit, hiker traffic for this trailhead had been backed up down the freeway, so it felt extra special to have the Instagram-famous vista all to ourselves.
As we made our way back to Portland, we circled around the White Mountains National Forest. Along the way, we spied Mount Washington (Agiocochook), Crawford Notch, and impressive/massive Bretton Woods Ski Area.
Stay: For our final two nights in Boston, we had a three-bedroom apartment in The Conrad building. You couldn’t beat its location right across the street from the Park Street Church and Boston Commons.
Day Six: Explore Boston and Cambridge
For our final full day in New England, we explored Boston pretty much on whim. Our only scheduled activity of the day was a free tour of Harvard University in Cambridge. As a result, we all took our first-ever ride on the Boston T!
Eat: After staying in one of the oldest hotels in America, we lunched at the oldest restaurant in America: Ye Olde Union Oyster House. I expected the restaurant to be a bit of a tourist trap, but we really had a lovely meal here. Even if my Boston broiled scrod wasn’t particularly flavorful (that’s the nature of scrod!), the restaurant’s pre-Revolutionary building alone makes it a worthy central Boston dining option.
Waypoints: We started the day with a wander through Boston Public Garden. I loved seeing the famous “Make Way for Ducklings” statue without any seasonal attire on! In Cambridge, we paid our regards at Car Talk Plaza and took a student-led tour of Harvard. After lunch, we walked the northern part of the Freedom Trail and had a delicious Boston cannoli taste-off.
Lessons Learned From Our New England Fall Trip
I took to heart a lot of the lessons learned from my Coastal Carolina Road Trip and worked really hard not to “overstuff” the itinerary. I think I was mostly successful . . . at least there wasn’t much dissent among the ranks! We had enough time to really enjoy the itinerary activities in a focused, unhurried manner. Still, spontaneity was not really a possibility.
That said, some things were a little too spontaneous. Instead of planning to grab lunch on our train ride from Boston to Portland, I should have stocked up in Boston. Talk about wasted opportunity to enjoy some Italian bakery treats!
A good indicator of an excellent trip is wishing it was longer. Ideally, this trip would have been at least 10 days. How I wished we’d had more time in Franconia. Despite spending two nights here, we barely explored it. If I could do it again, I’d add another night in Portland, a full day of exploring in the Franconia area, and at least one night in Vermont. Woodstock, VT – I’m coming for you next!
I also wished I’d booked a morning class at King Arthur Flour to avoid driving twisty, unknown New England country roads in the dark. We survived, but 100%, my eyes are getting older and I’m sure choice comments such as, “Where’s the stop sign?” were very reassuring to my passengers.
Lastly, if you’re going to do an autumn weekend walkabout on any college campus, check the events schedule first! It was fun to see Dartmouth, but if we’d realized it was homecoming weekend, we would have skipped it. At least parking in the municipal garage was free!
Other New England Fall Activity Ideas
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