I am someone who firmly believes you should be present and enjoy the current season. In late July, I noticed the first “is anyone else already dreaming of fall?” blurb on my Substack feed and was tempted to toss my phone out the window. While fall is my favorite season (I will die on this hill), it bothers me to see people wishing for September when we’re still in the midst of peak summer. Can no one slow down enough to enjoy a good thing when it’s happening anymore?
That said, I do understand the need to plan ahead — especially when you’re hoping to visit during peak season. New England is worth visiting any time of the year, but even I understand the appeal of early autumn. People from across the globe trek here every October with binoculars and cameras in hand, ready to watch what happens when shorter days and cooler temperatures tell trees to stop making chlorophyll. The green fades away, revealing hidden yellow, orange, and red hues in its wake. We (affectionately) call these people leaf peepers.
If you’re planning a fall foliage trip, I have some opinionated ideas on where to go. This list focuses on smaller towns and places some of you may know, some of you may not. Now let’s get into it.
Portsmouth, New Hampshire in the Fall
I’m always struck by how easy it is to underestimate Portsmouth. The cobblestone streets deliver exactly what you’d expect from a New England coastal town, but the food and drink scene is where it really gets interesting. Start at the Wilder for cocktails, then drift down Bow Street and pop into one of the many restaurants there for a light bite when the sun’s out and the harbor’s glittering. Row 34 is an institution for good reason; the seafood is fresh, and the menu fluctuates with the seasons. If you’re visiting on a weekend, end your night out on the back patio at Gaslight with live music and a glass of whatever local beer you’ll find on tap.
While Wentworth by the Sea is technically in New Castle, it’s a quick 10-minute drive to downtown Portsmouth and worth considering if you’re looking for higher-end accommodations. Don’t miss dinner overlooking the ocean at Latitudes, where you’ll quickly understand why people fall for New England in the first place. If you’d rather stay within walking distance of the action, there are other options available, such as the Inn Downtown (aptly named). Whatever you decide on, pack a warm sweater and a pair of sunglasses. Portsmouth in the fall is the best kind of weather; crisp enough to feel cozy, yet warm enough to actually sit outside all afternoon.
Stowe, Vermont in the Fall
Traveling to Stowe in October isn’t exactly revolutionary. You’ll find this small town at the top of every “Top Fall Destinations” list, and for good reason. Unlike the coastal towns on this list, Stowe sits in the mountains — which means if hiking is part of your fall trip, there’s plenty to explore here.
For a place this size, there’s a surprising amount of great dining. Plate focuses on seasonal ingredients with a Vermont-meets-California vibe. Harrison’s is popular too, but what you won’t find mentioned elsewhere is Edson Hill. I’m dying to stay here, but would happily settle for a dinner reservation. Picture this: sleeping in, spending an afternoon exploring the ember-lined walking trails on the property, enjoying a beer on an Adirondack chair, jacket drawn in close, then closing out the day with a cozy, farm-to-table meal. Sounds pretty good, right?
Although my perfect day at Edson Hill is, at this point, aspirational, what I can actually speak to is this: the best nights in Stowe are often the cozy nights in. Pizza delivered straight to your Airbnb, wrapped in blankets, passing around red wine and board games while the leaves turn outside. If you do venture out, there are breweries worth the walk, such as The Alchemist, Von Trap, Idyletime, and Stowe Cider. There’s truly something for everyone in this quaint Vermont town.
Camden, Maine in the Fall
Despite spending a lot of time in southern Maine growing up, I haven’t really ventured much into the Midcoast region. That changes come October. I’ve spent countless hours researching for our trip, and although we’re not spending the night in Camden (PTO is tight for me this year), I’m excited to spend an afternoon galivanting here.
The small town sits right where the mountains meet the sea, meaning you’ll get both the fall foliage and the harbor charm all in one place. The downtown is walkable, filled with galleries and independent shops, and appears to have all the markings of a quintessential New England town (minus the crowds, since the internet hasn’t caught on just yet).
In terms of dining, I’ve heard nothing but good things about Long Grain. Chef Ravin “Bas” Nakjaoen is a multiple James Beard Award nominee, and the menu is Thai-focused with influences from Singapore, Vietnam, and China. I’ve been instructed to order the mussels in coconut-lemongrass broth and the spicy “Night Market” noodle soup. 40 Paper is the answer if you’re looking for handmade pasta and flatbreads in a historical mill building, with a menu that changes based on what local fishermen and farmers bring in that week. Sounds a bit niche, but honestly, who here isn’t looking for that?
If the weather cooperates, get your blood pumping and hike Mount Battie for striking views. If it doesn’t, walk the harbor and call it a day.
Lake Winnipesaukee in the Fall
Lake Winnipesaukee is my happy place. My grandparents bought a home here in the 80s, then my parents bought a lakehouse here in the 2000s, meaning I basically grew up here alongside my sister and eight cousins. This isn’t just any rinky-dink lake; it’s the largest lake in New Hampshire, with about 300 miles of shoreline and 365 islands. What does all of this mean for you, as a tourist visiting in the fall? Foliage. Lots and lots of foliage.
What also sets Lake Winnipesaukee apart are the views — framed by the Belknap, Ossipee, and White Mountain ranges. In all my years, I’ve never seen a lake more beautiful. In early fall, the lake quiets, the water drops, and the surrounding mountains turn from emerald green to a sea of reds, oranges, and yellows. While everyone’s fighting for August reservations, locals will tell you, don’t sleep on September.
Wolfeboro’s got the historic downtown if you need it. But honestly? Rent a house if you can. Get out on the water. Rent a boat, and putz along the shoreline with an afternoon cocktail. Swim at sunset. Make s’mores by a campfire. That’s the whole point.
Until next time, New England.
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