A beautiful town near Cape Cod, Wellfleet is an ideal tourist destination for the summers. Beaches, hiking trails, biking, or a visit to the town museum, the town is replete with unique experiences. While Newcomb Hollow Beach, Cahoon Hollow Beach, and White Crest Beach are perfect for surfing or swimming, the Gull Pond Beach is more suited to families with paddle boats and kayaks for rentals. There is also the Province Lands Bicycle Trail or the Cape Cod Rail Trail for those who enjoy the outdoors. Besides, you can check out the Wellfleet Flea Market or the famous October Wellfleet OysterFest. With so many options, you are sure to get a holiday well spent in Wellfleet.

Sandwich gets its name from the seaport of Sandwich in Kent, England. Once a community of Native Americans, the town was eventually settled by Europeans and became a thriving commercial hub. Today, its bygone era can be witnessed through the historic homesteads that dot its quaint landscape, such as the Benjamin Nye Homestead that dates back to the 18th Century. For outdoor enthusiasts, Sandwich is home to the Oak Crest Cove Park, which features a skate park and tennis courts. Sandwich Glass Museum is another spectacular attraction to witness rare glass and glassworks.

Lexington is a charming town in Middlesex County. Located close to Downtown Boston, Lexington is famous for being the site where the first shots of the American Revolutionary War were heard. Steeped in Native American and colonial history, the town is also the site of the historic Battle of Lexington, touted as the first battle of the Revolutionary War. Owing to its historic significance, Lexington is also home the iconic Minute Man National Historical Park. Other landmarks and attractions include the Old Belfry, Buckman Tavern, and the Hancock-Clarke House.

Gloucester is a charming city in Essex County on Annisquam River whose history dates back to the time when it was the site of a Native American settlement. Eventually resettled by English colonists, the city thrived as a commercial hub and shipbuilding center over the centuries. Today, Gloucester is known for its quaint charm, with its landscape dotted with little shops, art galleries, and seafood restaurants. Art buffs are in for a treat as they can visit the home of Fitz Henry Lane and explore his works at the Cape Ann Museum. Other unique attractions include pristine beaches, Annisquam Harbor Lighthouse, and Eastern Point Lighthouse.

Located in Bristol County, Westport is a serene little waterside town. Named so for being the westernmost part of Massachusetts Bay Colony, Westport thrived in the early 19th Century as a shipyard and a cotton milling town. Thanks to its location on the Westport River, the town is now a popular tourist attraction that makes for an idyllic visit. Visitors can explore beaches such as Horseneck Beach State Reservation and South Shore Beach, tour local attractions such as the Sakonnet Lighthouse, and taste local food and culture at the vibrant shops, eateries, and galleries.

Hadley was settled as a town in 1659. This little place in Hampshire County was once a Puritan settlement before it gradually transformed as an agricultural town and finally, a quaint tourist village that is big on experiences. Its open-field farming landscape is steeped in history, which can be explored at museums and historic houses. The Porter-Phelps-Huntington Museum explores a resident family's history through interesting artifacts, while the Hadley Farm Museum is home to an incredible collection of farming vehicles and other exhibits.