Start from 16 curated places around Dewey Beach, DE, then choose the recommendations that fit your guests.
Restaurants & cafés
The Starboard
The undisputed anchor of Dewey Beach's social scene, The Starboard runs a legendary Sunday brunch with a build-your-own Bloody Mary bar that draws people from up and down the coast. By evening it turns into a lively music venue with live bands on the deck. The Orange Crush cocktails — fresh-squeezed OJ, vodka, triple sec — are the unofficial drink of summer.
Woody's Dewey Beach Bar & Grill
A no-frills beach bar that takes crab cakes seriously — they've won Best at the Beach more times than locals can count. The patio seating is dog-friendly and the vibe is reliably laid-back compared to the bigger venues up the strip. Portions are generous and prices stay reasonable for a beach town.
Trails & outdoors
Junction and Breakwater Trail
This 6-mile rail-trail runs through coastal scrub forest along the southwestern edge of Cape Henlopen State Park, connecting Rehoboth Beach and Lewes. It's mostly flat and paved, making it accessible for cyclists and walkers, and shaded by mature trees that offer real relief on hot summer days. From Dewey it's a short hop north to the Rehoboth trailhead.
Gordons Pond Trail
Inside Cape Henlopen State Park, this flat out-and-back trail runs about 3.2 miles each way along the brackish Gordons Pond, flanked by Atlantic dunes on one side and tidal wetland on the other, with a raised boardwalk over the marsh at the north end. Piping plovers nest in the dune cordons seasonally, and Great Blue Herons are practically permanent fixtures. The crushed-stone surface handles bikes as well as foot traffic.
Things to do
Bottle & Cork Live Concerts
The Cork stages live music in Dewey nearly every night from Memorial Day through Labor Day, booking a mix of regional touring bands, tribute acts, and the occasional bigger name who knows the beach circuit. The crowd ranges from twenty-somethings to veterans of the Dewey scene who've been coming for decades. It's loud, packed, and entirely the point of being in Dewey.
Dewey Beach Watersports
The main outfitter for bay-side activity in Dewey, offering jet ski rentals, pontoon boat rides, banana boat runs, sunset cruises, and guided kayak tours from their bayside dock. The sunset cruise is a genuinely pleasant alternative to spending the evening at a bar, and staff are patient with first-timers on the jet skis.
Landmarks & sights
Dewey Beach
Dewey's mile-long Atlantic beach is narrower and more social than the wide strands to the north — blankets practically touch in peak summer, and that communal energy is part of the appeal. The surf breaks reliably for bodyboarders, and the lifeguarded swimming area runs the length of the main strip. At low tide, the packed sand makes for a good strolling surface.
Rehoboth Bay (Dewey Bayside)
The sheltered bay side of Dewey is where watersports happen — calm, warm water makes it ideal for stand-up paddleboarding, kayaking, and windsurfing. Multiple outfitters along the bayside road rent equipment by the hour or half-day. The flat water is forgiving for beginners, and guided kayak tours wind around Thompson Island through salt marsh.