The Most Picturesque Small Towns In New England

As the “Birthplace of America,” New England’s reputation for old-world charm is a quintessential value embedded in the region. From quaint coastal villages with historic waterfronts to magnificent mountain ranges with award-winning ski resorts, visitors can expect a dazzling fusion of history, culture, and breathtaking natural scenes.

This intoxicating beauty permeates through every corner of New England, making it one of the most celebrated regions in the country for tourism. In 2020, Scotsman Guide reported that Maine alone brought in over $6 billion of tourism-related revenue, while other New England states like Vermont drew in nearly $3 billion. From the centuries-old structures to ancient waterways sculpted by time, New England promises sights and experiences that keep millions coming back time and time again.

Whether you are planning ahead for your next winter retreat or looking to book a more spontaneous coastal weekend away in 2024, the region is a four-season paradise with something for everyone. To experience these world-famous charms, here are seven of the most picturesque New England towns to get you started.

Montpelier, Vermont

Also known as “America’s Smallest Capital City,” with just over 8,000 residents, Montpelier, Vermont, exudes a fabulous small-town feel. The Hallmark town takes its cozy, mom-and-pop atmosphere very seriously, going so far as to keep big franchise businesses at bay. It is the only state capital without a McDonalds, Starbucks, or Walmart. Instead, you will find adorable locally owned businesses, restaurants, and museums like Bear Pond Books, The Three Penny Taproom, and The Susan Calza Gallery.

The town transports its visitors to simpler times in other ways as well, with historic sites like the restored State House. The Greek Revival structure is famously one of the oldest and finest preserved government buildings in the country. As for nature, even history extends to Montpelier’s dazzling outdoors, with attractions like Hubbard Park, the town’s largest and oldest green space, established back in 1899. With over 7 miles of hiking trails (and skiing trails in the wintertime), countless picnic areas, and an impressive 54-foot stone lookout tower, history and nature meld together for a magical New England experience in Montpelier.

Stowe, Vermont

Around a half hour’s drive from Montpelier, Stowe is another Vermont town with stunning natural scenes in every season. Surrounded by Spruce Peak and Mount Mansfield (Vermont’s tallest mountain), whether you visit in winter for the snowy slopes or summer for the wildflower hills, postcard views are with you every step of the way.

With 12 lifts, 116 trails, and an average of 314 inches of snowfall every year, the Stowe Mountain Resort is a winter wonderland for skiing enthusiasts. Mount Mansfield is equally gorgeous in the summer, though, and it is best viewed from the Gondola SkyRide or gorgeous hiking paths like the Sunset Ridge Trail. Other enchanting hiking paths include the Bingham Falls Trail, which leads to a beautiful cascade, and the Stowe Pinnacle, which rewards hikers with phenomenal views of the surrounding mountains. If the jaw-dropping views on this hike look familiar, that is because this is one of the most photographed spots in the entire state.

Meredith, New Hampshire

Making our way to New Hampshire, the breathtaking Lakes Region town of Meredith has one of the prettiest waterfronts in all of New England. Hugging the shores of beautiful Lake Winnipesaukee, New Hampshire’s largest body of water, this spirited waterfront community has some truly special sights and experiences.

While Meredith’s surrounding foliage is especially dashing in the fall, the town’s waterfront scenes are picture-perfect year-round. The 7-acre wooded Swasey Park is highly recommended in the warmer months, and it is one of the best places to appreciate Merideth’s lake views. There are also various kayak rental services in the area to take advantage of, like the nearby Wild Meadow on Winnipesaukee.

To see even more of Lake Winnipesaukee’s splendor, visitors can hop aboard the MS Mount Washington. Whether you take a narrated tour or a dinner cruise, the sights from this historic paddle steamer are exquisite. Back on land, lakeside Meredith Village is a darling commercial center with cute local businesses like the Bleu Waves Art Gallery and Hermit Woods Winery.

Lincoln, New Hampshire

Over in New Hampshire’s majestic White Mountains, the underrated alpine town of Lincoln is a gateway to endless outdoor adventures. This former logging town now thrives as a tourist destination, and nature lovers come here by the thousands. Its highlight attraction, drawing the most visitors by far, is Franconia Notch State Park. Adventure Journal magazine rates it the second-best state park in the United States, so rest assured, you are in for some magical sights.

The Franconia Notch mountain pass stretches from the Flume Gorge to Echo Lake, whose picturesque beach features the Mt. Lafayette and Cannon Mountains as its backdrop. Whether you stop for a swim, rent a pedal boat from the park, or stroll the borders of this stunning alpine lake, the fresh air and mountain views make any time here beyond worthwhile. As for the gorge, you will want to book a reservation ahead of time since the self-guided hike is extremely popular and spots are not guaranteed. Open from late May to late October, the 2-mile trail passes waterfalls, moss-covered gorge walls, and some really beautiful boardwalks.

Ogunquit, Maine

Heading to Maine’s southern coast, Ogunquit is a memorable beach town with one of the longest stretches of sand in the state. For 3 years in a row, the 3-mile shore was voted one of the top 25 beaches in the US by TripAdvisor's Travelers Choice/Best of the Best. Along with having one of the least rocky beaches in Maine, Ogunquit’s award-winning shore is a crowd-favorite due to its warm tides from the adjacent Ogunquit River.

With a beach this great, you can see why the town’s name translates to “beautiful place by the sea” in the Abenaki language. Its beauty is also a huge reason why the town of just over 1,000 residents swells to over 80,000 from May through September. But beyond these gorgeous shores, Ogunquit’s thriving arts scene also entices its fair share of crowds. Some notable attractions include the Ogunquit Museum of American Art, Ogunquit Playhouse Theater, and The Front Porch Piano Bar & Restaurant.

Bucksport, Maine

Voted USA Today’s #1 Seaside Small Town in 2021, Bucksport is another award-winning Maine community with stunning waterfront views. Located along a curve in the winding Penobscot River, the waterway is an anchoring feature of the town. The sights can be taken in on the Penobscot River Paddling Trail or from land on the mile-long Bucksport Waterfront Walkway. Here, visitors can also appreciate views of historic Fort Knox and the Penobscot Narrow Bridge.

But for the ultimate sightseeing experience, you will want to head to the Penobscot Narrows Bridge & Observatory. Famous for being the tallest public bridge observatory in the world, visitors can relish in 437-foot-high 360° views of the river, Penobscot Bay, and distant western mountains. Open from May to October, this one-of-a-kind experience is exhilarating and inspiring for all ages.

Mystic, Connecticut

For those who love towns with a story, the historic seaport village of Mystic, Connecticut, offers a picturesque look into the past. Located along both sides of the Mystic River (the two halves joined by the Mystic River Bascule Bridge), the town was once a thriving Connecticut seaport and shipbuilding center. Today, it is famous for upholding its maritime heritage with attractions like the Mystic Aquarium and Historic Downtown.

Visitors can learn even more about the town’s fascinating past at the Mystic Seaport Museum, the largest maritime museum in the country. Going above and beyond the typical gallery exhibit, the Mystic Seaport Museum features an interactive 19th Century Village with a shipyard. Here, visitors can explore the world’s only remaining whaling vessel: the Charles W. Morgan, built in 1841. Visitors can also hop aboard the Sabino, a historic vessel built in 1908, for a waterfront ride along the museum or a longer downriver cruise.

Final Thoughts

As the “Birthplace of America,” New England continues to live up to its heritage by celebrating the best parts of its past and embracing the brightest parts of its present and future. No matter the season, the picturesque region boasts gorgeous nature, fascinating historical landmarks, and some of the cutest downtowns and Main Streets in the country. Whether planning your next winter vacation on the slopes of Mount Mansfield or booking a historic river cruise aboard Mystic’s famous Sabino, the sights, sounds, and experiences are an endless delight.