This forested western Massachusetts region—which hugs the Connecticut River and includes towns like Amherst, Greenfield, and Northampton—has a dual personality: It’s quiet and quaint, but also boasts a lively cultural scene. “There’s so much to do,” says Tanya Costigan, owner of Westfield-based Bowties and Butterflies Event Planning.
When it comes to charm and tradition, Martha’s Vineyard takes the (wedding) cake. “The combination of history, rolling hills, and the ocean, with what happens when you get all your loved ones on an island for the weekend, creates magical memories,” says Patrie Grace, owner of the Vineyard-based firm With Grace.
Escapism is the appeal here. Just try walking by the Bellevue Avenue mansions without daydreaming about living in Rhode Island’s historical playground for the rich. “It takes you away,” says Christine Ellingwood, owner of Warwick-based Planned to Perfection.
The wide open spaces in this part of Connecticut make for memorable celebrations, says Amy Cagginello, of Amy Champagne Events, in Milford. “The amount of land you have up this way is so unusual,” she says. “You almost forget where you are. Things are done more slowly. It may take longer to get places, but it’s beautiful.”
This tranquil, woodsy New Hampshire area is perfect “for people looking for a natural, outdoor setting that is truly beautiful in any season,” says Emily St. Pierre, owner of Concord’s All the Fuss Events.
“Ocean breezes, harbors, fishermen working right on the wharf, beautiful shops, and delicious food—[this Maine spot] has quintessential charm, but it also has your big-city necessities,” says Amber Small, a planner with Portland-based Sweetest Thing Weddings.
“We’re surrounded by mountains, and the peak fall foliage coupled with the historic properties makes for an amazing escape,” says local event pro Janet Dunnington of this Vermont town. But it’s not only an ideal autumn getaway: “It’s what we call a winter wonderland,” she adds.