9 Prettiest Small Towns In New England
When it comes down to picture-perfect countryside in the United States, New England easily tops the list. From snow-covered mountains to well-preserved historical villages and classic coasts that line idyllic seaport towns, the overall vibe is truly unmatched. The region is one of the top destinations in the country to experience the famous fall foliage. Visit in September or October, as New England is painted in bright, warm shades. From the stunning natural diversity of Acadia National Park in Maine to the TV show-worthy streets of Washington, Connecticut, New England unfolds like a scenic masterpiece.
Stowe, Vermont
Tucked into the staggering Green Mountains, Stowe is a renowned winter wonderland, but it's a dream all year long. Welcome the snowy season by spending time on the slopes at award-winning Stowe Mountain Resort, where you can ski and snowboard at top speeds down iconic Mount Mansfield, Vermont's highest peak. In summer and fall, the resort offers hiking trails and a climbing wall, as well as the option to ride the gondola to the peak for a bit shopping, sightseeing, and snacks. The Vermont Ski and Snowboard Museum is also open year-round, with ever-changing exhibits to keep things interesting. Past collections include Searching for Vermont's Lost Ski Areas and Scott Lenhardt: Artistic Contributions to Burton Snowboards.
Vermont towns are the epitome of shopping at rustic general stores and supporting the locals. The Country Store on Main is a one-stop shop for clothing and a large assortment of home goods. Purchase some new cookware, table linens, holiday decorations, or an adorable apron to add a touch of "down on the farm" flair to any space. As the top producer of maple syrup in the United States, it would be silly to leave Vermont without some of its liquid gold. Located on the legendary Route 100, stop at Stowe Maple Products for 100% pure maple goodness. Maple caramels, maple cream, and a quart of maple syrup naturally make the best souvenirs from Stowe.
Nantucket, Massachusetts
Nantucket is a secluded storybook coastal village that encompasses old-world charm. Step back in time and walk the cobblestone streets lined with pre-Civil War buildings. Built sometime in 1686, The Oldest House on Sunset Hill, also known as the Jethro Coffin House, offers a one-of-a-kind glimpse into the past. Tour the family home to get a feel for a bygone era. Reconstructed to resemble a 1700s herb and vegetable garden, step out the back of the house to the kitchen garden. For more history, venture down Main Street to the Hadwen House. Dating back to 1846, the mansion is steeped in elegance, and a striking example of Greek Revival architecture. Today, the residence operates as a museum showcasing Nantucket's past, and the grounds house a serene Victorian-style garden.
Located approximately 30 miles from the shores of Cape Cod, Nantucket is a tranquil Massachusetts retreat. As a gorgeous waterfront marvel, the island naturally has some of the most pristine beaches. Catch some rays and soak up some much-needed vitamin D on 40th Pole Beach. Let the kids splash in the warm, shallow waters and go barefoot through the silky sands. Before leaving the island, take some photos in front of the Great Point Lighthouse. Originally built in 1784, it underwent two reconstructions and is a notable Nantucket landmark proudly lighting up the Atlantic Ocean.
Westerly, Rhode Island
Tucked along the Connecticut border, Westerly is an elegant Rhode Island town that looks like a postcard. Stroll through the downtown area, getting lost among the fine eateries and welcoming shops. Mingle and unwind at Perks & Corks, a refined martini lounge and coffee shop with an undeniable romantic atmosphere. Loosen up with a classic Cosmopolitan or spiked coffee in the dimly lit lounge, then stay awhile and relish in a luxurious lifestyle at Ocean House. Sitting atop Watch Hill, get pampered at this stunning Victorian retreat. The hotel boasts a AAA Five Diamond and Forbes Five-Star rating and, if that's not enough of a draw, the buffet dining room faces Taylor Swift's famed Rhode Island mansion.
First settled in 1661, Westerly's history is a lengthy chapter, and the town decorates Rhode Island with numerous reminders of its past. Take a ride on the Flying Horse Carousel, one of the oldest in the country and believed to have been built in 1876. Travel to a different time at the Babcock-Smith House Museum, a 1734 Georgian showpiece. Search through the permanent collection within the house, featuring a staircase with intricate designs and a cooking fireplace complete with vintage cookware.
Essex, Connecticut
Essex is a quintessential New England town, hugging the Connecticut River. Rows of meticulously maintained Federal and Colonial-style buildings line the streets, enhancing the town’s rich history. Book a walking tour to take a peek at the historical highlights. Venture around downtown, learn about hometown heroes at the River View Cemetery, or discover the village of Centerbrook. Rest up at the Griswold Inn, welcoming visitors since 1776. Each uniquely decorated guestroom is draped in comfort with an antique touch.
From serene waterfronts to rolling hills and lush greenery, New England is a textbook example of endless scenic vistas. Hop aboard the vintage Essex Steam Train and take a cruise on the Riverboat to watch the Connecticut landscape come to life. For two and a half hours, take in the unspoiled views of Selden Neck State Park and pass by the towns of Deep River and Chester. If you really want to make a night of it, book a luxurious evening on the Dinner Train, where you can indulge in a four-course meal while on a voyage through the immaculate Connecticut River Valley.
Woodstock, Vermont
The entire state of Vermont comes alive in the fall, and Woodstock stands out as a top contender for the ultimate autumn getaway. As the crisp, clean air blows through this enchanting region, visitors flock to Woodstock for leaf-peeping and small-town magic. Take a hike up Mount Tom for an impressive panoramic view of the trees bursting with fiery reds and vivid shades of oranges and yellows. Grab some souvenirs and fill up on fall treats at the Apples and Crafts Fair and Food Truck Festival in October.
Woodstock looks like it is straight out of a Hallmark movie, with rolling farmlands and winding country roads. Just a short walk from the town center, Billings Farm and Museum sparks curiosity and offers unlimited activities. Find out about the workings of a dairy farm and see how the gardens are maintained. Make a new furry friend and wave hello to the sheep, goats, chickens, steers, and horses. Come back again for one of the special events, such as the Harvest Celebration, Family Thanksgiving, and The Magic of Maple.
With around 100 covered bridges sprinkled throughout Vermont, they are an essential photo opportunity in any season. The Middle Covered Bridge is notorious for attracting photographers. Capture its splendor during the snowy winter, blossoming spring, or colorful fall.
Washington, Connecticut
Washington is a rural gem with all the comforting vibes. The town is wrapped in a majestic pattern of cozy farmlands, lush forests, and a quiet ambiance. As the inspiration for the beloved show Gilmore Girls, it is no surprise that Washington checks all the boxes for the typical New England lifestyle. Be the main character yourself and stroll around the downtown core with coffee in hand from Marty's Cafe, then continue the adventure next door, where you can find a new favorite at The Hickory Stick Bookshop. This indie bookstore has proudly been a local favorite for over 70 years. Browse the titles, or stick around for one of the bookstore's events, such as a book signing, poetry reading, or monthly book club meeting.
Every corner in Washington is like a living canvas, draped in captivating backdrops. Averill Farm is a popular destination for seasonal excitement. Pick up some maple syrup, potatoes, pumpkins, gourds, or jams from the middle of August until the end of December. Commemorate the fall season with a freshly baked pie, apple cider donuts, or an afternoon of apple picking. Bask in Connecticut's natural radiance at Hollister House Garden. The timeless space is layered with rows of stunning flowers and flourishing plants. Find a quiet spot among the acres for introspection, meditation, or relaxation.
Bar Harbor, Maine
As the name suggests, Bar Harbor is a seaside treasure with sparkling waters, enchanting sunsets, and top-tier dining. Savor the taste of Maine's seafood, straight from the source at The Terrace Grille. Nothing beats a classic New England clam chowder, steamed lobster, or lemon-seared haddock. Finish off with blueberry pie, a classic Maine staple, and call it a night well spent. Visitors looking to shake things up a bit should head to Havana. With an ever-changing seasonal menu to keep things interesting, Havana offers a taste of Maine with Latin flavor.
Embrace the slow-paced New England life, perfectly paired with a salty sea breeze and raw beauty. Trek through the boundless wilderness at Acadia National Park. With approximately 158 miles of hiking trails and 72 miles of paved and carriage roads, it is easy to see why Acadia is a visitor favorite. From easy and accessible hikes to challenging climbs, the park features expeditions for all skill levels. Touch the sky with an exhilarating mountain climb or reconnect with nature during a deep forest exploration. Be one of the first in the country to watch the sunrise on the summit of Cadillac Mountain. The views from way up high are ethereal.
Salem, Massachusetts
Salem earned its spot on the map due to the hysteria and significance of the Salem Witch Trials. Today, the city still exudes a spooky atmosphere, naturally. Feel the eerie aura at The Witch House, one of the very few homes left in Salem that had a direct connection with the Witch Trials. The residence formerly belonged to Judge Jonathan Corwin and is currently a museum showcasing historical artifacts from the 17th century. Take a deep dive into the happenings of the Salem Witch Trials at the Salem Witch Museum. The exhibits depict the chronology of all the happenings from beginning to end.
The spirit of Halloween and all things related lingers in Salem year-round. Stock up on supplies at Crow Haven Corner, Salem's oldest witch shop. From crystals to occult books and candles, the store has everything to make the world a little more magical. Kick it up a notch and book the Airbnb right above the establishment for a bewitching good time. October is a bustling time in Salem, Massachusetts. Join the crowd for the Salem Night Faire at Pioneer Village. Hear chilling ghostly tales by the fireside, be mesmerized by the live performances, browse through eccentric vendors, and warm up with hot cider.
Peterborough, New Hampshire
Peterborough is a hidden New England wonder in the shadows of the Monadnock Mountains along the Contookook River. The sleepy town is timeless, with tree-lined streets, charming brick buildings, and local businesses flashing with character. Often overlooked in the story of New England, New Hampshire’s Peterborough offers a secluded haven for those seeking to escape the crowds. Curl up with some sought-after home cooking at the Peterborough Diner. Since 1949, the restaurant has maintained an old-timey appeal. Dig into an egg sandwich or stack of buttermilk pancakes, all made with love. After breakfast or lunch, pick up a treat from Sweet Macaron. Take pleasure in these French pillow-soft treats with a delicate, crisp shell. Try a classic like vanilla or be daring and try the Fruity Pebbles, Creamsicle, or French Toast macarons.
Peterborough is a noteworthy gathering spot for fellow artists and creatives. As the inspiration behind Thornton Wilder’s play, Our Town, this quaint New Hampshire town continues to brim with culture and curb appeal. Since 1933, the Peterborough Players have entertained visitors and locals alike with professional productions. The current up-and-coming summer performances for 2025 include Native Gardens, Hay Fever, Spelling Bee, and Dial M for Murder. Be in awe while browsing paintings at Gary Shepard Fine Art. Specializing in landscape, the pictures allow nature to come alive.
Experience the Beauty of New England
Bring a camera and venture to some of the prettiest places in New England. Bask in luxury at Ocean House in Westerly, Rhode Island, or get a feel for a stereotypical New England lifestyle in Essex, Connecticut. Head to Bar Harbor, Maine, for the feast of a lifetime, including some of the freshest seafood you'll find anywhere, and then work it off with a hike at Acadia National Park. Dive into the rich arts and culture scene in Peterborough, New Hampshire, or ski the epic slopes of Vermont's Green Mountains. Head to one of the country's premier destinations for the occult and learn about the chilling witch trials in Salem, Massachusetts. No matter how you choose to explore, New England is a flawless blend of adventure, aesthetics, and a memorable time.
