Oak Bluffs in August

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Oak Bluffs in the thick of August 2026: Circuit Avenue crowds, the harbor at full capacity, gingerbread cottages dressed in flags, the Flying Horses in its 150th year, and the food stops that carry the season.

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Gingerbread cottages with flags flying on an August morning in Oak Bluffs

Circuit Avenue packed with August visitors

Looking down Circuit Avenue past Murdick's Fudge and the Strand, peak-season crowds

Oak Bluffs harbor at full capacity, dinghies weaving between the moorings

Boats stacked into every corner of the harbor on a busy August day

The Dream Catcher heading out of the harbor

Sunflowers riding on the bow, a summer-day detail from the harbor

Blue Heaven, an 1867 cottage at the entrance to the Campground

An 1868 gingerbread cottage in the Campground

The Flying Horses Carousel, 150 years old in 2026

Reaching for the brass ring at the Flying Horses

The poster for the carousel's 150th birthday party, held July 25

The Ritz Cafe sign on Circuit Avenue, pouring since 1944

Highlands General, the new year-round market in the old Linda Jean's space

The Sweet Life Cafe on upper Circuit Avenue

Nancy's on the harbor on a busy August day

Summer ice cream stop in Oak Bluffs

Giordano's, serving fried clams and pizza since 1930

The information booth by the harbor

The welcome sign at the edge of town, summer 2026

A fare-free VTA bus rolling through town

Seaview Avenue along the water

A dog keeping watch from a boat in the harbor

The balloon mural in downtown Oak Bluffs

An easy August day in Oak Bluffs

One of the painted alleys near the harbor

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