8 Adorable Small Towns In Massachusetts

Few states embody the idea of “adorable” quite like Massachusetts does. Across its coastal towns and mountain communities, you will find fairytale-like cottages, colonial-style reenactment villages, and even the shortest lighthouse in New England! The holiday season is a wonderful time to visit as well, as some of the towns host festive events and holiday markets. If you are looking to explore some of the coziest and most adorable towns in Massachusetts this year, these eight towns will steal your heart.

Oak Bluffs

Between its colorful cottages and vintage carousel, Oak Bluffs feels like a town out of a classic fairytale. At its heart are the Gingerbread Houses, a collection of vibrantly painted, pastel homes downtown that were built in the 19th century. After taking a stroll through this whimsical neighborhood, head over to the Flying Horses Carousel, the oldest platform carousel in the country, which has been in the Oak Bluffs community since 1884. On the carousel, you’ll find hand-carved wooden horses, each of which is brightly painted. Keep in mind that this carousel is open seasonally. Once you start getting hungry, you can grab a bite at Lookout Tavern, a waterfront restaurant that serves oysters, lobster, fried fish, and more.

Sandwich

Nicknamed “The Town That Glass Built,” Sandwich thrived early on due to the presence of a large glass factory. Today, the town continues to honor its glassmaking heritage through local glass studios and museums. Travelers can learn about this colorful glass history at the Sandwich Glass Museum, which has been preserving and exhibiting glassworks since 1925. Interested in buying a piece of your own? Check out the McDermott Glass Studio to browse their gallery of glasses and vases, and catch live glassblowing demonstrations from Wednesday through Friday. While in the area, visitors can enjoy a day of hiking at the Old Sandwich Game Farm Wildlife Management Area, which has hiking trails that wind through salt marshes, pine and oak forests, and shrubby fields.

Provincetown

Home to the oldest continuous art colony in the United States, Provincetown’s art scene is unlike any other in Massachusetts. The Provincetown Art Association and Museum is one of the best places in town to experience this art firsthand, featuring five galleries and regularly rotating exhibits that showcase work from the area’s artists. You’ll find an abundance of galleries throughout town as well, many of which are concentrated along Commercial Street. Four Eleven Gallery is a brilliant one to visit, exhibiting work from both Provincetown and Outer Cape artists. Travelers who spend the night in town can lodge at the Pilgrim House, a historic inn from 1810 that has a weekend piano bar and several cozy guest rooms to choose from.

Sturbridge

In Sturbridge, visitors can travel back in time at Old Sturbridge Village, New England’s largest outdoor museum. Spanning over 200 acres with 40 historical buildings, it brings the past to life through costumed historians portraying the daily lives of early New England residents. You can continue to enjoy the outdoors at Wells State Park, a 1,400-acre public park that has 12 miles of hiking, biking, horseback riding, and cross-country skiing trails. To conclude your day of exploration, enjoy a meal at Sturbridge Porterhouse, a steakhouse set in a historic horse barn that whimsically embraces a quaint horse stable atmosphere.

Rockport

Rockport is home to one of the most painted buildings in the country: Motif #1. Although the original red fishing shack was destroyed in the Blizzard of 1978, a charming replica stands in its place, which travelers can visit on Bradley Wharf. In May each year, the town also throws Motif No. 1 Day to celebrate this iconic building. Activities during this festival include a Plein Air Motif No.1 competition, food trucks, music, and more. If you are looking for a unique way to explore the city, consider signing up for a charter with Rockport SeaVenture, which offers 90-minute tours of the Rockport Harbor with a local and knowledgeable captain.

Falmouth

With the holidays coming up, you won’t find a town much more charming than Falmouth. From December 5th through 7th, the town decks itself out in Christmas cheer during the Holidays by the Sea Weekend. Activities during this festival include a lighthouse holiday open house, Christmas caroling, a village holiday stroll, and more. If you are starting to think about holiday gifts, stop by the Falmouth Art Center’s Holiday Market, which will take place between November 22nd and December 24th and feature over 100 vendors. Travelers with a sweet tooth can grab some handcrafted chocolate at Ben & Bill's Chocolate Emporium, where they can purchase rich chocolates, candies, and homemade ice cream.

Lenox

Lenox is a laid-back town in the Berkshires surrounded by farms and historic country estates. Some of the area’s local farms are open for visits, such as High Lawn Farm, a local creamery just south of town that produces artisanal cheeses and ice cream that guests can try on site. Lenox is also home to The Mount, the historic estate of author Edith Wharton, where visitors can tour the house, grounds, and gardens throughout the year. If you are looking for a historic place to stay, you will love the Brook Farm Inn, which is set in an adorable, 1865 Victorian home.

Nantucket

Sitting just off the coast, Nantucket has that quintessential New England vacation feel, complete with lighthouses, beaches, and seafood. There are three lighthouses on the island to visit, one of which is Brand Point Lighthouse. This light is a mere 26 feet tall, making it the shortest in New England! There are several places to enjoy an afternoon of sunbathing and swimming, such as Jetties Beach, which has a gentle surf and amenities like public restrooms, showers, changing rooms, and a seasonal restaurant. For some lobster, fried fish, or a clambake, Sayle’s Seafood is a beloved dining establishment, selling both raw fish and ready-to-eat seafood that guests can enjoy on its waterfront deck.

Sometimes the best escape is getting lost in a small, storybook-like village. Massachusetts is the perfect place to do so, as the state is absolutely brimming with adorable destinations. If you are looking for a bit of nostalgia, towns like Oak Bluffs are excellent destinations, while others, like Provincetown and Rockport, have fun and peculiar art scenes. So start planning your trip and get ready to experience a bit of that small-town magic for yourself!