7 Underrated Small Towns to Explore in Massachusetts

The charming and diverse New England state of Massachusetts is the ideal vacation destination for history lovers, as it has a rich background dating back to its founding in the late 1700s. It is also bordered by both the Atlantic Ocean and the Gulf of Maine, making it an outdoor and water-lover's paradise. Not only does Massachusetts have a rich Revolutionary War history, colonial architecture, distinguished universities, and sandy beaches, but it also boasts many small, underrated towns that are ready for exploration.

Rockport

Quaint Rockport is known for being a thriving art colony and is home to more than 30 galleries featuring work from local and regional artists. The coastal town is situated on the very tip of the Cape Ann peninsula on the Atlantic Ocean, about 40 miles northeast of Boston. Rockport is the quintessential seaside retreat, and it has something to keep visitors entertained for all four seasons, whether you want to spend time on the water or attend an exciting special event, such as the Rockport Jazz Festival.

If you are visiting during the warm summer months and want to dip your toes in the ocean, check out Long Beach, Front Beach, or Cape Hedge Beach. Rent an ocean kayak at a local rental shop, such as North Shore Adventures and Outdoor Center, or book an adventure tour. If you are an arts and culture lover, you can catch a live musical performance at the Shalin Liu Performance Center.

Provincetown

Nestled on the northern tip of scenic Cape Cod, pretty Provincetown is the ultimate vacation destination for ocean and beach lovers of all ages. The town is where the Mayflower landed in 1620 and is home to the famous Pilgrim Monument, which offers sweeping views from 350 feet above. Provincetown also boasts the country's oldest continuous art colony and hosts a variety of annual special events, including the Provincetown Carnival and Women's Week.

This coastal oasis also has a thriving foodie scene, and presents a mix of casual and gourmet eateries, many serving fresh seafood with plenty of local flavor. It is a haven for artists and art lovers, and boasts a large number of galleries, including the Adam Peck Gallery, Alden Gallery, and Art Love Gallery. Provincetown also has a rich history dating back to the 17th Century, and you can explore it in detail at the Provincetown Museum. The Sea Space Marine Discovery Center is located downtown on Whaler's Wharf, and provides hands-on activities for visitors of all ages.

Lenox

Lovely Lenox is another underrated small town worth exploring and getting to know, whether you are staying just a few nights or a few weeks. Even though Lenox is part of the thriving Pittsfield Metropolitan Statistical Area, it has a charming small-town feel. Lenox is known for its arts and cultural scene and is the summer home to the Boston Symphony Orchestra, as well as the site of Shakespeare and Company.

If you are a history lover, you will delight in all of Lenox's museums and historical attractions, including The Mount: Edith Wharton's Home. The community is also home to the Frelinghuysen Morris House and Studio, the Ventfort Hall Mansion, and the Gilded Age Museum. Nature enthusiasts won't want to miss the Berkshire Botanical Garden and the Mass Audubon Pleasant Valley Wildlife Sanctuary.

Oak Bluffs

Situated on the scenic and prestigious island of Martha's Vineyard, picture-perfect Oak Bluffs is the perfect place to spend any type of vacation, especially if you love the ocean. The seaside retreat is known for having the largest marina on the island as well as a bustling downtown. The Oak Bluffs Marina offers convenient access to the entire island and is a favorite among both local and out-of-town boaters and anglers.

There are so many fun things to do in Oak Bluffs year-round that it may be hard for visitors to narrow them down. If you are in the area during the warm summer months, spend some time at one of Oak Bluff's sandy beaches, including Inkwell Beach and Joseph Sylvia State Beach. Not only can you enjoy the sand, sun, and sea, but you can also view the colorful Victorian gingerbread-style cottages the area is known for.

Edgartown

Another classic Martha's Vineyard seaport village, eye-catching Edgartown may get overlooked for bigger cities, but don't let size fool you here. It is a quintessential New England seaside respite, complete with a historic downtown filled with local shops and eateries, Old World charm to spare, and relaxing beaches. Situated on the eastern side of the island, Edgartown is the ideal spot for travelers looking to relax and unwind.

If you are visiting during October, don't miss the Martha's Vineyard Food and Wine Festival, a renowned event that Edgartown hosts each year. One of the top attractions is the historic Edgartown Harbor Lighthouse, which is just a short walk from downtown. The community was settled in 1642 by whaling captains, and many of their restored homes can be seen during a historic walking tour.

Great Barrington

Located in the southern part of the Berkshires, a rural mountain region in Western Massachusetts, Great Barrington welcomes visitors with majestic views, a thriving downtown, and several popular attractions and recreational areas, such as Monument Mountain, the Butternut Ski Area and Tubing Center, and Mount Washington State Forest. Although Great Barrington is tucked away in the state's scenic mountains, it is known as a spectacular place to ski, snowboard, and partake in other winter activities.

The Great Barrington Cultural District is home to a mix of casual and gourmet restaurants serving local farm-to-table fare, unique boutiques and other shopping opportunities, and cultural hotspots such as the Historical Society Town Museum. Other local attractions to put on your "must-see" list are the Bidwell House Museum and the Guthrie Center.

Orleans

The quaint Cape Cod community of Orleans ranked number two on Coastal Living Magazine's 2017 list of "Happiest Seaside Town in America," and for good reason. Situated between charming Nauset Beach on the Atlantic side and Cape Cod Bay's calming Skaket Beach, Orleans offers something for everyone, whether you are traveling to the area on a girls' weekend getaway or a summer family vacation. Downtown Orleans is filled with a mix of quirky boutiques, art galleries, and eateries serving fresh local seafood, among much more.

Orleans is one of Massachusetts' designated cultural districts. It boasts the Artist Cottages at Orleans Market Square, a collection of colorful wooden huts in which local artists showcase their work, and the Academy of Performing Arts. Popular outdoor activities include swimming, fishing, boating, and even surfing during the summer months.

While Massachusetts is best known for its thriving cities filled with modern amenities and attractions, it is the state's smaller, less well-known communities that welcome visitors with historical sites, cultural institutions, and plenty of local flavors to take in. Whether you crave a relaxing seaside respite or a few days or weeks in the mountains, you will find it in Massachusett's small, underrated towns.