This is your place to plan the ultimate getaway. From the rolling hills of the Berkshires in Western Mass all the way to Provincetown, the “best gay resort town”, and also the number one destination for same sex weddings in America. In between, you’ll find Northampton, the hippest small town imaginable; the dizzying arts and culture and night life of Boston; and last but not least, the eclectic, postcard-perfect communities of the Cape and Islands. Off the beaten path, you’ll find hiking and biking to your heart’s content, small town charm and big city culture, and a collection of wonderful historic sites unrivalled by anywhere else in the country. Let’s go!

In Massachusetts, everyone is welcome. We’re not only history-makers as one of the most advanced states in the country in terms of LGBTQIA+ rights legislation, today we’re one of the most LGBTQIA+-friendly vacation destinations. Learn more about what makes Massachusetts special.



As Massachusetts’ capital city, Boston has long been an epicenter of LGBTQIA+ rights and culture. Boston boasts one of the largest LGBTQ+ populations on the East Coast, with historic neighborhoods like the South End and Jamaica Plain welcoming LGBTQIA+ residents and visitors alike. Boston Pride is held each June, and the Equality Trail celebrates the city’s history of LGBTQ rights year-round.

Explore LGBTQ activities and history in Boston


Jiminy Peak, Hancock

Hampshire County

Western Massachusetts is a place where everyone is truly free to be their authentic selves. There’s no better place for those who want to feel the inclusivity of a big city in a small town environment.

Explore Hampshire County


Martha’s Vineyard

Whether you’re getting married, on your honeymoon, or just traveling solo, Martha’s Vineyard has something for everyone. Pristine beaches, art galleries, and family-friendly activities as well, each of the six towns in Martha’s Vineyard have something special to offer.

Explore Martha’s Vineyard


Rainbow flags fly high above Commercial Street in downtown Provincetown, Massachusetts.



Located at the tip of Cape Cod, “P-Town” has been a premiere destination for the LGBTQIA+ community for decades. For many, it’s a tradition to travel to Provincetown for Memorial Day Weekend to officially kick off the summer. Carnival, a weeklong festival held each August, has been celebrated annually since 1978 and today attracts over 90,000 visitors. Autumn events include Women’s Week, held each October; Fantasia Fair, which celebrates anyone who identifies as trans; and of course, Halloween. There’s even a holiday-themed festival each December!

Explore Provincetown



With a perfect score from the Human Rights Campaign’s equality index, Salem is one of the most LGBTQIA+-friendly destinations in the country. In addition to its famous Halloween celebrations, Salem hosts a festival each month, including the North Shore Pride Festival every June.

Explore Salem