Dewey Beach Travel Guide: Things to Do, Best Time to Visit & Itinerary

Dewey Beach is often called “A Way of Life” by its loyal visitors, and it doesn’t take long to understand why. Crammed onto a narrow strip of sandbar just one mile long and two blocks wide, this Delaware town manages to pack an incredible amount of energy into a tiny footprint. To the east, the Atlantic Ocean crashes against wide, sandy beaches; to the west, the calm waters of Rehoboth Bay offer spectacular sunsets. It is a place of duality, shifting effortlessly from a family-friendly sunbathing destination by day to the mid-Atlantic’s premier nightlife hub when the sun goes down.

While its larger neighbor, Rehoboth Beach, is known for its boardwalk and vintage charm, Dewey is the rebellious younger sibling. It is less about fudge shops and more about open-air decks, live rock and roll, and water sports. The town has a unique, walkable layout where you can watch the sunrise over the ocean, walk two blocks, and watch it set over the bay, making it a paradise for those who want to maximize every second of their beach weekend.

A Tale of Sand and Sound

Dewey Beach’s history is relatively young compared to other Delaware coastal towns. Originally just a stretch of dunes, it wasn’t incorporated until 1981, primarily so the locals could manage the booming summer crowds themselves. This independent spirit is still felt today. The town is famous for its “Skim City” reputation; the steep slope of the beach creates a shore break that is world-renowned for skimboarding. If you visit in summer, you will see pros and amateurs alike throwing their boards into the wash, a tradition that has deep roots here.

Culturally, Dewey is defined by its music. The town is a regular stop for major touring bands who play at legendary venues that feel more like giant backyard parties than formal concert halls. Despite its party reputation, the town maintains a strong community feel, hosting events like the Golden Jubilee and the massive Greyhounds Reach the Beach festival, where the town is literally taken over by thousands of rescue dogs.

The Icons You’ll Want to See

The Starboard - No trip to Dewey is complete without visiting this landmark. Famous for its pile of orange peels (used for fresh crushes) and the “Shark Tank,” it’s the social heart of the town. Prices vary, but expect $10–$12 for cocktails. It is located right on Route 1.

Indian River Inlet Bridge - located about 2 miles south of Dewey, this stunning cable-stayed bridge is a photographer’s dream, especially at night when it is illuminated in blue. It connects the north and south sides of the Delaware Seashore State Park. Free to drive over, or small park fees to park underneath.

Rehoboth Bay Marina - situated on the bay side, this is the hub for renting jet skis or pontoon boats. It is also the perfect spot to watch the sunset away from the bar crowds. Rentals start around $100/hour depending on the vessel.

East of Maui - A classic local surf shop that embodies the Dewey vibe. It is the place to buy a skimboard, rent a kayak, or just get advice on the tides. Located centrally on Route 1.

Planning Your Visit

Getting to Dewey Beach usually involves driving, as it sits directly on Coastal Highway (Route 1). Traffic on summer weekends can be intense, so try to arrive on a Thursday night or early Friday morning if possible. Once you are in town, park your car and leave it. The town is incredibly walkable, and the Jolly Trolley provides a fun, open-air shuttle service that runs continuously between Dewey and Rehoboth Beach for a small fare ($3–$5), saving you the headache of finding parking in both towns.

Packing for Dewey requires beach essentials, but also a “going out” outfit. The vibe is casual, flip-flops are acceptable almost everywhere, but the nightlife scene is energetic. Don’t forget bug spray if you plan to be on the bay side at dusk, as the marsh mosquitoes can be aggressive. Most importantly, download the ParkMobile app before you arrive; Dewey Beach has no parking meters, and everything is paid via the app with strict enforcement.

Dewey Beach is intense, loud, and incredibly fun. Whether you are there to dance until 2 AM at the Bottle & Cork or to wake up at dawn for a quiet paddle on the bay, it delivers an authentic American summer experience that keeps people coming back decade after decade.