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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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Plate 01 Gingerbread cottages with flags flying on an August morning in Oak Bluffs -
Plate 02 Circuit Avenue packed with August visitors -
Plate 03 Looking down Circuit Avenue past Murdick's Fudge and the Strand, peak-season crowds -
Plate 04 Oak Bluffs harbor at full capacity, dinghies weaving between the moorings -
Plate 05 Boats stacked into every corner of the harbor on a busy August day -
Plate 06 The Dream Catcher heading out of the harbor -
Plate 07 Sunflowers riding on the bow, a summer-day detail from the harbor -
Plate 08 Blue Heaven, an 1867 cottage at the entrance to the Campground -
Plate 09 An 1868 gingerbread cottage in the Campground -
Plate 10 The Flying Horses Carousel, 150 years old in 2026 -
Plate 11 Reaching for the brass ring at the Flying Horses -
Plate 12 The poster for the carousel's 150th birthday party, held July 25 -
Plate 13 The Ritz Cafe sign on Circuit Avenue, pouring since 1944 -
Plate 14 Highlands General, the new year-round market in the old Linda Jean's space -
Plate 15 The Sweet Life Cafe on upper Circuit Avenue -
Plate 16 Nancy's on the harbor on a busy August day -
Plate 17 Summer ice cream stop in Oak Bluffs -
Plate 18 Giordano's, serving fried clams and pizza since 1930 -
Plate 19 The information booth by the harbor -
Plate 20 The welcome sign at the edge of town, summer 2026 -
Plate 21 A fare-free VTA bus rolling through town -
Plate 22 Seaview Avenue along the water -
Plate 23 A dog keeping watch from a boat in the harbor -
Plate 24 The balloon mural in downtown Oak Bluffs -
Plate 25 An easy August day in Oak Bluffs -
Plate 26 One of the painted alleys near the harbor -
Plate 27 The seawall walk between the ferry wharf and the town beach -
Plate 28 The stone jetty: half fishing spot, half front-row bench for boat traffic -
Plate 29 The Islander settling into the harbor at golden hour -
Plate 30 The evening current on Circuit Avenue by the Ritz -
Plate 31 Lake Avenue corner at full August capacity -
Plate 32 The dockside restaurants filling up as the light goes pink -
Plate 33 Circuit Ave Extension: bike lane, rental row and the Jetty sign -
Plate 34 Seaview Avenue rolling down toward the water -
Plate 35 The sightseeing tour stand between departures -
Plate 36 Big Dipper: coffee, donuts, bagels, hot dogs and ice cream on one wall -
Plate 37 Island Hoppers with a spare bike parked on the roof -
Plate 38 The new Jetty Beach House sign: raw bar, grill, cocktails -
Plate 39 Curio, coastal curiosities under the eucalyptus -
Plate 40 Vineyard Caribbean Cuisine, open sign glowing -
Plate 41 Giordano's take-out menu wall, air conditioned and proud of it -
Plate 42 Midnight Taco with the patio full and lanterns up -
Plate 43 Midnight Taco sign framed in paper lanterns -
Plate 44 The neon that has fed a thousand ferry lines: pizza to take out -
Plate 45 Sharky's neon in the window, a ballgame reflected beside it -
Plate 46 Summercamp and the campground lanes dressed for Illumination week -
Plate 47 The Island Queen summer schedule board at the dock -
Plate 48 The Rhode Island boat boards here: sandwich board at the ramp -
Plate 49 Boarding the Quickwater at the seawall -
Plate 50 A 1950s Plymouth aging gracefully outside a campground cottage -
Plate 51 Aalia's Coffee, the fish-shaped sign on the blue shingles -
Plate 52 The fireworks banner that outlived its show: cancelled for 2026, back next year -
Plate 53 Vineyard's Ice Cream and Coffee Co. with a full porch again -
Plate 54 A quiet morning at the Inkwell, lifeguard stand waiting for the crowd. -
Plate 55 Cruising Sea View Avenue past the Sea View on a flat-calm August day. -
Plate 56 Sea View Avenue along Ocean Park, parking full, wharf straight ahead. -
Plate 57 A cruiser bike outside a candy-colored cottage, hydrangeas in bloom.
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