Experience the Best of Rehoboth Beach, Delaware in 3 Days

“All-American” and “old-fashioned” are the terms frequently used to describe Rehoboth Beach, Delaware. Indeed, the town of Rehoboth presents like a movie set of a 1950s-era beach town. There’s the broad and weathered boardwalk, lined with taffy shops, arcades, photo booths and those old-timey fortune-telling machines. There’s stately Rehoboth Avenue, with even more souvenir shops and, on the maze of little streets around it, some really good restaurants.

But the Rehoboth area also boasts some wild spots, including the Delaware Seashore State Park to the south. You also shouldn’t miss the energetic bars and clubs in rollicking Dewey Beach, just 2 miles down the road.

As always, check for travel restrictions and closures before planning your trip.

Friday: Stroll the Boardwalk and Downtown Rehoboth

The boardwalk in Rehoboth is the anchor of the entire area. Start your morning at the Breakfast Guru, which, as its name suggests, is the authority on morning meals. Try the “Steak ‘n Eggs” — that’s 10 ounces of rib-eye – or go for the “Veggie Breakfast Burrito.”

Then head for Funland, a family-friendly assortment of 20 rides and 11 games of chance and skill, located directly on the boardwalk. The circa-1962 pavilion has a kitschy charm — much like the rest of downtown Rehoboth.

Funland’s main rival is Zelky’s, the self-proclaimed “best family arcade in Rehoboth,” with three locations on the boardwalk. The third contender is Ryan’s, an 18-hole mini-golf course located on top of Ryan’s Beach Shop with views over the ocean.

Our best arcade advice: Try one venue every day for three days (and be prepared to take home an assortment of plush toys and other tacky prizes).

Next, wander the shops along Rehoboth Avenue and, around it, the maze of streets. All are extremely strollable, so ditch the car (there’s a public parking lot not far from the boardwalk). Along with the obligatory stores selling bikinis and beach towels, the town also boasts a few high-end galleries, including the Stuart Kingston Gallery, an auction house for fine art.

Browseabout Books is a very good independent bookstore right on Rehoboth Avenue, offering beach reads as well as literature and a nice selection of books and toys for kids. And, fair warning, you will feel compelled to buy a kite — can’t explain it, but it’s a thing here — so stop into Rehoboth Toy & Kite Company, also on Rehoboth Avenue.

With arcade fun and kite shopping out of the way, it’s time for the beach. Luckily, it’s just steps from the boardwalk and stretches as far as the eye can see. There are crowds on the sand closest to town, but walk just a few minutes (or, depending on the day, a few minutes more) in either direction and find yourself in empty expanses of beach and people-free swimming and surfing.

Throw on your real clothes — shorts and T-shirts are fine almost everywhere, but you will need shoes — and begin your evening food crawl at Brewings & Eats, choosing from the menu of a dozen beers on tap and ordering up a plate of fried pickle chips while listening to live music.

For dinner, visit the hip Asian-fusion restaurant Stingray Bar & Grill for entrées like seared-tuna tacos and wood-fired oven pizza. Top off the night with ice cream from the Ice Cream Store, whose creamy, dreamy flavors include the popular “Bacon Maple Crunch.”

Saturday: Discover Dewey Beach — by Day and Night

Kick off your Dewey Beach day at Sunrise Restaurant, a spot serving simple, diner-style breakfasts. The town’s a little sleepy in the morning — and you’ll see why if you stick around for the nightlife. You might think of Dewey as Rehoboth’s sassy little sister. Really little — the year-round population is fewer than 400 souls — and really sassy, thanks to a main drag packed with more bars than restaurants.

Expect to have the normally crowded beaches almost entirely to yourself. And Dewey’s wide stretches of sand are glorious, especially if you take a long walk south until you run into the Delaware Seashore State Park, where you’ll share the sand with only gulls and shells. (Alternatively, you can drive and park.) While you’re there, visit the park’s Indian River Life-Saving Station, now a museum.

Head back to town for lunch (Mama Maria’s pizza is a fave), then consider an afternoon of water sports.

For instance, you can take skimboarding or surfing lessons at Alley Oop Skim, a Dewey institution since 2000. Or set sail with the crew from Dewey Beach Parasail (ages 6 and up, reservations required). And if you already know what you’re doing, rent a paddleboard or a kayak from Delmarva Board Sport Adventures, where windsurfing lessons are also on the menu.

To continue the day’s surf vibe, have dinner at Nalu (the word means “wave” in Hawaiian), an open-air restaurant serving poke bows and shrimp tacos.

Down for Dewey’s nightlife scene? Then head on over to the Bottle & Cork, considered one of the best venues for live rock music in the area. Established in 1936, the club books both major acts (Dave Matthews has played there) and local talent.

Sunday: Bike a Beachside Park

Start your day at the Royal Treat, billed as the oldest restaurant in Rehoboth and serving traditional breakfast fare — eggs, pancakes, sausages— as well as elaborate ice cream concoctions (note to self for later in the day). While you’re in town, pick up sandwiches at Frank & Louie’s for your picnic in the park.

Then, cycle off your breakfast at Cape Henlopen State Park on the coastline north of town, where you can borrow (for free!) bikes at the Seaside Nature Center. Cruise the park’s trails, visiting Fort Miles Museum, once a World War II coastal defense site, and stopping for a picnic at what’s called “the Point,” an overlook with views of dunes, lighthouses and the ocean.

If cycling isn’t your speed, the trails are walkable and the park also offers a sandy beach with lifeguards that’s a favorite among surfers and skimboarders.

Next, shake off the sand and grab a spot in line for arguably the area’s best restaurant, the Henlopen City Oyster House. Your “spot” is a virtual one — you’ll get a text when your table is ready — and you may be glad for the wait, because you can pass the time in the bar area, where as many as eight varieties of oysters are served.

The “Oyster Sampler” is popular, loaded up with two each of all eight. Grab a local beer (the Dewey Beer Co. could not be more local) or a glass from the carefully curated wine list. The dinner menu also puts locally caught seafood and Delaware-farmed foods to good use, and everyone loves the lobster mac and cheese.

This thoughtful approach to food is also practiced at Henlopen’s sister restaurant, the Blue Hen, just down the street — same local ingredients, same awesome beer list, but a smaller (and equally tempting) menu.