When it comes to fall and winter in the United States, nothing quite beats the charm of a New England town. Think Stars Hollow or Dawson's Creek (or Twin Peaks, if you're really going there), there's something about the charm of a small town that you can't quite beat. Especially when the season is just ripe, the leaves begin to go several shades of vermillion, and they fall and swirl all around you. A cup of piping hot chocolate, your best Uggs (yes, they're still deserve a place in this world), and a map, it's all you need for your perfect Hallmark movie experience.
While we can't quite guarantee you the love story that comes with it (it can still happen, we just can't guarantee it), we can provide our best recommendations for the towns in New England you should hit up for the best fall and early winter getaways. Because it really 'tis the season…
Stowe
Northern Vermont's Stowe has, what Outbound Stowe's Director of Sales, Molly Quinn Pasic, describes as "classic New England charm with endless opportunities to explore." She tells HELLO! that local highlights like the Stowe Recreation Path elevate it beyond being just a "fall" town, although that reputation certainly doesn't hurt.
"The town itself has a wonderful sense of place, with a charming downtown ideal for leisurely strolls and discovering local favorites," she explains. "It becomes more than just a foliage trip; it is a full weekend immersed in the spirit of the season." She cites activities like "apple picking, farm dinners, cider tastings, craft breweries" as other attractions of the town.
As for what you can get up to while there? "Outbound Stowe has communal fire pits where you can toast marshmallows or enjoy a drink under the stars." You could also take a relaxing beat by the West Branch Little River or hit up Lamoille Valley Bike Tours.
Boston
While not the "quaint" town you might be imagining, Leon Bolivar, Director of Marketing at the Omni Boston Hotel at the Seaport, reasons that the Massachusetts capital is the way to go to kick off any New England trek. "One of the best ways to experience fall is by starting your journey in Boston's Seaport District," he tells us.
You could partake in the city's "waterfront walks framed by autumn colors," and especially noting Boston as the ideal centerpoint to take off to any number of charming towns that are as little as 90 minutes away, like Concord, Rockport or Portsmouth.
As for sights and recommendations for the area: "Visitors staying at the Omni Boston Hotel at the Seaport can take advantage of blue bikes or nearby public transit, making it easy to explore Boston and beyond without a car. And bring your camera – the city skyline against the fall foliage is something special."
Nantucket
Keeping it in Massachusetts for a bit longer, we have the island of Nantucket, where we find a different kind of fall activity in the mix – scalloping. Greydon Hotels' General Manager Garison Beale, in particular, is a big fan, saying: "It's truly one of the only places in New England where you can experience this, and even more special doing it 30 miles out at sea." Scalloping season opens in October.
He has a simple explanation for why tourists and locals alike flock to the region for the reason: "It's the beauty and the romance of it. Whenever you look at a picture, see a movie, or read a story about autumn, you're almost always looking at a New England town. Tourists often tell us they feel that same camaraderie every time they visit our island, especially during the fall months."
It's that feeling of community, in particular, that he says attracts people to Nantucket and other towns like it. "New Englanders look forward to fall every year, knowing the warmth and sense of community it brings to each small town."
Cape Cod
If we're taking it to the water, Cape Cod is another waterside locale just ripe for exploration. In particular, Sea Crest Beach Resort's Director of Sales & Marketing Meghan Kelleher recommends the Upper Cape, for its "quieter, more relaxed version of the Cape once summer crowds fade." Don't worry, if it's foliage you seek, you'll still see it aplenty along the cape coast, or with a ride across the Shining Sea Bikeway.
If you're worried about not making the trip in time for the late September or early October fall weeks, you're in luck with Cape Cod, which finds the season really taking shape in late October and November. "Beyond the stunning foliage, New England's charm lies in its mix of small-town character, local harvest festivals, farm-to-table dining, and coastal beauty."
And it isn't just fall, either! "Fall also rolls effortlessly into the early winter season, when small towns like Falmouth start to sparkle with holiday lights, seaside strolls are crisp and peaceful, and ski towns up north begin to open for the season."
How to plan your trip — our experts' top tips
It always comes down to one thing – what you pack. Prime focus should be on layers and footwear. "Pack layers since the weather can shift quickly, and bring comfy shoes for walking or biking," Kelleher notes, with Beale similarly adding: "On Nantucket, for instance, a windy day can come out of nowhere, so you need to be sure that you have a good layering system."
Bolivar also mentions that if you're in Boston for the weekend, "comfortable walking shoes are a must for sightseeing," while Pasic emphasizes that it's all about scheduling, scheduling, scheduling. "Check the town's calendar to see what local events are happening during your visit so you can plan around something that fits your interests."
"Attending a community event is a great way to feel more immersed and experience the true spirit of the town. If you want to avoid larger crowds, consider visiting midweek."