12 Prettiest New England Towns in the Fall You’ll Love
Looking for the prettiest small towns in New England in the fall? I got you covered! This is hands down my favorite season to explore the region.
The leaves turn brilliant shades of red, orange, and yellow, the air is crisp, and every town feels extra charming. From quiet mountain villages to bustling coastal spots, there’s no shortage of places to enjoy the season.
In this guide, I’m sharing the most beautiful New England towns in the fall, including my go-to foliage destinations in Vermont, cozy White Mountains getaways in New Hampshire, and picturesque harbor towns in Maine.
Whether you’re planning a quick weekend trip or a longer New England fall road trip, these picturesque towns are guaranteed to give you all the fall vibes!
Disclaimer: Some of the links in this post are affiliate links, which means I may earn a small commission if you make a purchase, at no extra cost to you.
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Most Beautiful Small Towns in New England in the Fall
1. Stowe, Vermont
Stowe is one of the most famous New England towns in the fall, and for good reason. Surrounded by the Green Mountains, it’s packed with scenic drives, hiking trails, and postcard-worthy views.
Main Street is lined with boutiques, cafés, and restaurants, and the historic white church with Mount Mansfield in the background is a must for photos.
If you have time, take a drive along Smugglers’ Notch for winding roads framed by brilliant foliage. It’s hands down one of the most scenic fall drives in Vermont!
Stowe is also a great base for visiting nearby covered bridges and waterfalls, so you can easily fill a weekend here. For a fun fall treat, stop by Cold Hollow Cider Mill for fresh apple cider and warm cider donuts.
2. Camden, Maine
Camden is a coastal gem that looks even more beautiful in the fall! The harbor is filled with sailboats, the surrounding hills are covered in color, and the downtown streets are lined with independent shops and cozy cafes.
Walk along the waterfront, browse the local boutiques, then head to Mount Battie in Camden Hills State Park for sweeping views over the harbor and Penobscot Bay.
If you’re planning a Boston to Bar Harbor road trip, Camden makes an excellent stop along the way. It’s about halfway between Portland and Acadia National Park, so you can enjoy a night here before continuing up the coast.
In the fall, the mix of ocean views and foliage on the surrounding hills makes it one of the prettiest towns in New England to visit.
3. Woodstock, Vermont
Woodstock is often called one of the prettiest towns in Vermont, and it’s especially magical in the fall. The town green is surrounded by historic buildings, boutique shops, and inviting cafes, all framed by vibrant foliage.
Just a short walk from the center, you’ll find the Middle Covered Bridge, one of the most photographed spots in town.
A weekend in Woodstock is all about slowing down and enjoying the season. Visit nearby farms for fresh produce and maple products, take a scenic drive along the Ottauquechee River, or explore Billings Farm & Museum for a taste of Vermont’s rural history.
With its cozy inns and postcard-perfect views, it’s an easy favorite for a fall getaway in the USA.
4. North Conway, New Hampshire
North Conway is one of the best New England towns in the fall for a mix of foliage, mountain views, and small-town charm.
It’s the perfect base for exploring the White Mountains, with easy access to scenic drives like the Kancamagus Highway and routes through Crawford Notch.
In town, you’ll find plenty of restaurants, shops, and cafes, along with the historic Conway Scenic Railroad, which offers foliage train rides through the mountains. For even more views, drive up to Cathedral Ledge or hike one of the nearby trails.
Whether you’re just passing through or staying a few nights as part of a New Hampshire fall road trip, North Conway is a must-visit during peak leaf season.
5. Ogunquit, Maine
Ogunquit is a charming seaside town that’s just as lovely in the fall as it is in the summer. The summer crowds are gone, the weather is still pleasant, and the coastal scenery is even more striking with touches of autumn color.
Take a walk along the Marginal Way, a scenic path that winds past rocky cliffs and sandy beaches, or spend time exploring the shops and galleries in Perkins Cove.
It’s also a great stop to include on a coastal Maine road trip. You can pair it with nearby Kennebunkport or continue north toward Portland and Camden.
Even outside of peak beach season, Ogunquit offers plenty of reasons to visit, from lobster shacks and seafood restaurants to sunset views over the Atlantic.
6. Jackson, New Hampshire
Jackson is one of the most beautiful towns in New England during the fall, known for its covered bridge, white steepled church, and surrounding mountain views.
The foliage here is incredible, and the small-town charm makes it feel like you’ve stepped into a postcard. It’s a quieter alternative to nearby North Conway but still close to scenic spots like Pinkham Notch and Mount Washington.
If you visit in October, you’ll also see the famous Pumpkin People displays scattered around town, with creative and often funny scenes set up by local businesses and residents.
Stroll through the village, check out local art galleries, and take a drive along Carter Notch Road for some of the best leaf-peeping in the area.
7. Manchester, Vermont
Manchester is a great stop on any Vermont fall road trip, with its mix of historic charm, mountain scenery, and plenty of things to do.
The town is home to outlet shops, cafes, and restaurants, as well as the beautiful Hildene estate, once the home of Abraham Lincoln’s son.
In the fall, drive up Mount Equinox Skyline Drive for sweeping views of the Green Mountains covered in vibrant foliage. You can also explore nearby hiking trails or visit local farms for fresh cider and donuts.
With its combination of outdoor activities and a lively town center, Manchester is an easy place to spend a full day during leaf-peeping season.
8. Bar Harbor, Maine
Bar Harbor is the gateway to Acadia National Park and one of the most popular New England towns in the fall. The mix of ocean views, colorful foliage, and charming downtown streets makes it a favorite for fall travelers.
Stroll along the Shore Path for stunning coastal scenery or wander the shops, cafes, and restaurants in the heart of town.
Fall is also a great time to explore Acadia without the heavy summer crowds. Drive the Park Loop Road, hike trails like Jordan Pond Path or Cadillac Mountain, and enjoy the brilliant mix of reds, oranges, and golds against the rocky coastline.
Whether you’re here for a weekend or as part of a longer trip through Maine, Bar Harbor delivers classic New England fall beauty.
9. Portsmouth, New Hampshire
Portsmouth is technically a small city, but it has the same charm and walkable feel as the prettiest New England towns in the fall.
The historic downtown is filled with brick sidewalks, independent shops, and great restaurants, all framed by colorful trees.
You can stroll along the waterfront, explore the gardens at Prescott Park, or tour Strawbery Banke Museum to see centuries-old homes.
Fall is also a great time to take a harbor cruise or enjoy one of the seasonal festivals happening in town.
With its mix of history, coastal views, and a lively main street, Portsmouth fits perfectly into a New England fall getaway.
10. Stockbridge, Massachusetts
Stockbridge is the definition of small-town New England charm, especially in the fall! The tree-lined streets are filled with historic buildings, quaint shops, and cozy cafes, all surrounded by the rolling hills of the Berkshires.
It’s also home to the Norman Rockwell Museum, where you can see original works by the artist who often painted scenes inspired by the town.
Fall is a great time to take a walk down Main Street, which looks much the same as it did in Rockwell’s famous holiday painting. You can also explore nearby hiking trails or drive to scenic overlooks for panoramic foliage views.
Stockbridge is an easy stop to combine with other Berkshire towns like Lenox or Great Barrington.
11. Meredith, New Hampshire
Meredith sits right on the shores of Lake Winnipesaukee and is one of the best spots in the Lakes Region to see fall colors.
The waterfront boardwalk offers beautiful views of the foliage reflecting on the water, and the town has a mix of art galleries, local markets, and spots to grab a coffee before heading out on the lake.
In the fall, you can take a scenic cruise with the M/S Mount Washington, explore nearby hiking trails, or drive around the lake for even more leaf-peeping views.
Meredith’s combination of lake scenery and vibrant foliage makes it a standout stop in New Hampshire’s fall season.
12. Salem, Massachusetts
Salem is one of the most famous New England towns in the fall, and October is when it truly comes alive. Known for its witch trial history, the town draws visitors from all over for its Haunted Happenings festival, themed tours, and historic sites.
Some of the best things to do in Salem in October include visiting the Salem Witch Museum, exploring the House of the Seven Gables, or simply wandering the cobblestone streets lined with 17th-century buildings.
If you don’t mind the crowds, the Halloween season is an unforgettable time to visit. For a quieter experience, plan your trip in late September or early November when the fall colors are still beautiful but the streets are less packed.
