7 Breathtaking Towns to Visit in New England

Bennington, Vermont

Chartered before any other town in 1749, Bennington, where Vermont likely began, is breath-takingly buried in history. The state's tallest structure, the 306-foot-tall Bennington Battle Monument, greets visitors right from the highway, reminiscing of the victorious battle that pivoted the American Revolutionary War into the American forces favor on the New England front. Old First Church, Vermon's oldest church in Bennington, dates back to 1762, while literary fans come to pay respects to the poet Robert Frost at the nearby cemetery, his last resting place.

Don't miss the notable Bennington Museum, proudly displaying the world's most extensive public collection of Anna Mary Robertson "Grandma" Moses' 20th-century folk art, among other antiques and artworks. Home to numerous venues and outdoor landmarks, five covered bridges, starkly red along the winding Walloomsac River, are part of its treasured past in the local county. Having grown as a cultural hub, Bennington's galleries, workshops, and live theater impress modern art fans while retaining an authentic New England feel that is unique to Vermont.

Eastport, Maine

The Down East town of Eastport is often overlooked as a gem along Maine's eastern seaboard. Retaining an opulent air of history with all the architecture on its own, pristine Moose Island, Eastport, is heart-wrenchingly picturesque from every corner. Many come to indulge in the freshest seafood served right out of the waters, including all kinds of fish and lobster, like at the Happy Crab. Old Sow Grill features monthly jazz and string jams, named after the iconic Old Sow here, one of the largest tidal whirlpools in the US, which inspires mysticism. Visitors can also take a water taxi to the peaceful Treat Island and enjoy the Sutherland Amphitheater for an al fresco moonlight movie or Horn Run Brewing, a classic favorite.

WaCo, the state's oldest diner from 1924, offers a filling breakfast for a daytime whale-watching charter with Butch and his crew at Eastport Windjammers or Shackford State Park's scenic hiking trails before a glass of wine over nibbles at Phoenix Fine Wines. Eastport's thriving art scene of unique local works is a smattering of shops and galleries along the historic Water Street. Don't miss the Eastport Arts Center for a classic music performance and a chance to chat and see the process of creation at StudioWorks. Home to a vibrant indigenous community willing to share insights and traditions, maybe you can meet some of them at Ole Hookers, a local cocktail bar.

Madison, Connecticut

While Mystic is often the star of the state, Madison is breathtaking in its simplicity—beloved among the East Coasters. Retaining a feel of authenticity and undiscovered, Madison feels like layered chocolate-coated candy bursting with flavors in a pretty wrap. Once listed as the only "Best Beach Town" in the whole state by Yankee Magazine, its outstanding beaches continue to mesmerize without crowds to spread out on the pristine sands, with clear surf lapping at your feet. From award-winning bookstores to art cinemas and tea emporiums, elegance is unmistakable in local aesthetics through coffee shops, cafes and restaurants, clothing boutiques, and gift shops.

On the other side of the pedestrian-friendly downtown, woodlands provide for a refreshing stroll with untouched trails, despite being so close to amenities that appeal to all tastes and interests. From an opulent waterfront hotel to several bed and breakfasts, Madison masterfully blends natural scenery into small town urban charm, like its E.C. Scranton Memorial Library and a large town green that anchor downtown. Hammonasset Beach State Park attracts new families, couples, and returning tourists for a pretty boardwalk between two miles of beaches, wetlands, and woodlands.

Monhegan Island, Maine

Some ten miles from the mainland of Maine, Monhegan is a scarcely square-mile-sized, rocky island town with only access by boat. Well worth it, the walkable town has been dependent on tourism and fishing since the 1800s. Visitors get treated to the local lifestyle, like fishermen retrieving catch from the lobster traps along the unpaved roads by the docks. From there, it is just a short stroll to the village heart and its most attractive feature, the breathtaking cliffs overlooking stunning coastal landscapes. Clustered on the third of the island, its lodging, gift shops, and refreshments, the remote island town appeal features unique saltbox architecture and imposing lighthouses.

Around the town, "wildlands" comprise nine miles of maintained hiking trails to ocean cliffs, the highest along Maine's entire coastline, with puffins, seals, and porpoises below the dramatic cliffs and whales in the distance. Attracting adventurers, respite seekers, artists, and photographers, visitors can join them with an easel or a picnic. Sample their work through welcoming studios and craft cooperatives that shed light on how this oceanside hike has been a destination for creatives since the mid-19th century to relish the isolated feel, recreate the staggeringly beautiful terrain, and share their inspiration. The Monhegan Museum of Art and History displays many such paintings and drawings en plein air.

Newport, Rhode Island

Newport, a classic New England harbor town with deep red brick streets and bustling outdoor markets, is truly breathtaking from every side, like its very own 10-mile coastal drive, a bikeable highway between the scenic coastline and beautiful parks! Once a favorite summertime playground for America’s wealthiest families during the Gilded Age, "City by the Sea" retains an opulent air that fosters a feel of intimacy and inspires artistry. Today, accessible for all to enjoy the meticulous preservation of over a dozen homes, including shoreside, Newport is a step into the time warp of the Age of Innocence and Moby Dick, the two worlds that all romantics dream of revisiting.

The sandy beaches here stay particularly quaint even in the summer, so dig your toes in the serenity of the Atlantic breeze, with just the right amount of sunshine to keep you daylong basking in relief. The 3.5-mile Cliff Walk is an invigorating adventure for couples or more moments in peace with your loved ones to soak in the panoramic ocean views, salty air, crashing waves, and those stunning Gilded Age mansions. Drenched in authenticity, Newport’s old-school ice cream and taffy shops delight kids of all ages, while historic seaside taverns reveal the local lifestyle like in the old days.

North Conway, New Hampshire

North Conway, “Best Ski Town,” delivers in all four seasons within the White Mountains of New Hampshire, with quaint antique shops, bookstores, and bakeries. Attracting everyone from adventurers and skiers to historians and photographers, the quaint town with gorgeous historic buildings overlooks the peaks right downtown. The breath-taking scenery prevails whether on an outdoor excursion, a culinary adventure, or a hunt for unique treasures along Settlers Green or Main Street in the village. The 34.5-mile Kancamagus Highway starts in Conway and cuts through White Mountain National Forest with magnificent fall foliage, while the 18-mile Presidential Traverse Trail presents a rigorous hike just an hour north.

Listed in the top 10 for “Best Small Town for Adventure,” its larger-than-life character features landscapes like the Cathedral and Whitehorse Ledges for rock climbers, many covered bridges in the area, and waterfalls. Schouler Park in North Conway Village, a local favorite for a weekend picnic or lunch break, offers free summertime concerts and a playground, while the water hole in the Saco River is great for a swim. Don't miss North Conway's historic train station straight from the Victorian age, with trains still coming and going along the Conway Scenic Railroad. The New England Ski Museum displays the history of skiing in the region, which ski bunnies can enjoy first-hand at Cranmore Mountain, with scenic chair lift rides, a mountain coaster, and a Mountain Adventure Park open in the warm season.

Siasconset, Massachusetts

Siasconset is tiny and often overlooked at the eastern end of Nantucket, about eight miles from the more popular town on the remote Nantucket Island. Seemingly a world of its own, the active enjoy access to the beachside town via a 6-mile Milestone Bike Path or a 9-mile Polpis bike path, alongside a shuttle service or a private bus. Overflowing with beach peas and rose gardens within white picket fences, the rows of classic New England saltbox houses follow you in the scented air on the way to the beach at the end of Milestone Road, with no amenities, just lifeguards.

Its renowned heavy surf adds a sense of drama to the otherwise quaint community, formerly a fishing village. Sconset, to locals, offers an all-dimensional experience of island life, from its storied past against the evoking panorama of the Atlantic Ocean to the rose-covered cottages jostling side by side with elegant new homes, with the picture-perfect blue ocean peeking in between. Home to the island's most scenic walk, ‘Sconset Bluff Walk starts from the village with views every bit behind its name, leading you north to the evoking views of the lonesome Sankaty Head Light.

Madison exudes an air of elegance with tea emporiums and boutiques, while "Sconset" is a former fishing village blending a quaint seaside lifestyle with drama evoking heavy surf against panoramic ocean views.

Don't miss North Conway's "Best Ski Town" historic train station straight from the Victorian age, and when in Eastport, it's home to the iconic Old Sow, one of the largest tidal whirlpools in the US. If you've ever wished you lived during the Age of Innocence or the Moby Dick era, Newport, RI, nails the feels.