4 Best Sights in Oak Bluffs, Martha's Vineyard

This 34-acre warren of streets is tightly packed with more than 300 gaily painted Carpenter Gothic Victorian cottages with wedding-cake trim; they date mainly to the 1860s and '70s, when visitors coming for Methodist revivalist services began to lease lots and build houses for summer use. As you wander through this fairy-tale setting, imagine it on a balmy summer evening, lighted by the warm glow of paper lanterns hung from every cottage porch. This describes the scene on Illumination Night at the end of the Camp Meeting season, which is attended these days by some fourth- and fifth-generation cottagers—and newcomers: some houses do change hands, and some are rented. Attendees mark the occasion as they have for more than a century, with lights, song, and open houses for families and friends. Ninety-minute tours of the area are conducted at 11 am on Tuesday and Thursday in July and August; the Friday night Sunset Concert Series on Tabernacle Green is always festive.

One of five lighthouses on Martha's Vineyard, the 40-foot structure was built out of cast iron in 1876 to replace an 1828 tower that burned down. The lighthouse is open seasonally on Sunday evenings around sunset; the views of Nantucket Sound from atop the bluff are spectacular. Parking is limited.

A National Historic Landmark, this is the nation's oldest continuously operating merry-go-round. Handcrafted in 1876—the horses have real horsehair and glass eyes—and brought from Coney Island in 1884, the ride gives children a taste of entertainment from an era before smartphones. Kids delight in trying to grab the brass ring for a free ride.

This 2-mile-long sandy beach has a view of Cape Cod across Nantucket Sound. Occasional food vendors and calm, warm waters make it a popular spot for families. Arrive early or late in high summer: the parking spots fill up quickly. It's best to bike, walk, or take the shuttle here. Amenities: parking (no fee). Best for: swimming.