Oak Bluffs is full of Victorian gingerbread cottages like this one dating to the 19th Century.

By Diane Vadino

Oak Bluffs is a vibrant town that's a change of pace from the more reserved Edgartown. It’s near pretty public beaches and has its own collection of adorable village shops, but the main attraction is the town’s gingerbread cottages — turreted, gabled, doll-like treasures only a few steps removed from a fairy tale. There’s also a museum devoted to the cottages’ history, with displays including stereoscopic pictures of the 19th-century Cottage City.

Kids will love the chance for a cone of locally made ice cream at Mad Martha’s followed by a few rounds on the 132-year-old Flying Horse Carousel, the oldest operating platform carousel in the country. Their parents, meanwhile, will be happy to spend the afternoon exploring Oak Bluffs’ many antique shops and galleries.

Mad Martha's
117 Circuit Ave.
Oak Bluffs, MA, 02557
(508) 693-9151

Flying Horses Carousel
33 Circuit Ave.
Oak Bluffs, MA, 02557
(508) 693-9481
$1.50 per ride