4) Westport, Massachusetts
In summer months, the trend is usually towards the north coast of Massachusetts. The little know gem of Westport rarely, if ever, makes the tourist destination lists. This south coast charmer is a lure, however, for some of Boston’s top chefs, who are known to frequently vacation here. Local produce, hand crafted cheeses and award-winning sparkling wines are among the bounty that draws them. There’s also a local brewery, where you’ll find a vibrant summer night life that includes live music concerts. It’s home to a modern contemporary art gallery that showcases the local talent and a quaint vibrant old world downtown with not one strip mall in sight. It also features an amazing wildlife sanctuary, stunning beaches and kayaking adventures. Horse Neck State Beach Reservation is the place to be if you’re into wind surfing, bird watching and hiking along the many trails. There’s a host of interesting eateries for a taste of the local seafood or rustic American fare. Lodging choices range from boutique hotels and local B&B’s, to luxury accommodations with some major hotel chains around or just outside of town.