Going for the 'Now' Factor
Dewey Beach is often described as Rehoboth's younger, bar-hopping sibling, and in fact the town wasn't incorporated until 1981, so it's only recently attained its legal drinking age. (The Bottle & Cork proudly advertises itself as having been founded in 1936, but back then it was a combination gas station/general store and spaghetti diner that got its ice from what is now Silver Lake.)
But Dewey's party-hearty image may be endangered by the widespread conversion of commercial property to increasingly upscale condos and hotels. With a moratorium on such conversions looming (and now in place), many popular retail and dining establishments, the Ruddertowne complex included, moved quickly to redevelop. So if you've ever wanted to do the Dewey, do it now.
(The flip side of the shift is that more year-round residents are giving Dewey Beach a new and more gentle sense of community, so we've included a few "adult" moments.)
It's worth noting that since most of the nightlife addresses are fairly close together and parking is limited, the Rehoboth-based Jolly Trolley (302-227-1197) runs along Route 1 from Ruddertowne to Silver Lake and on into Rehoboth; each trip is $2 before midnight and $3 until 2 a.m. Let that be your designated driver.
7:30 p.m. The Taco Toss at the Lighthouse in Ruddertowne (Dickinson Street and the bay) is a tradition too hilarious to miss, a cross between "Coyote Ugly" and "Where the Boys Are." (For those who call in well on Fridays, it starts at 4.) The crowd generally mixes with survivors of the outdoor calypso party across the parking lot at the Rusty Rudder (302-227-3888) and spreads out down the pier as the sun sets.
9 p.m. The Bottle & Cork (1807 Route 1; 302-227-7272) remains one of the best, and most eclectic, music clubs in the region: In the first two weeks of June, it will host Dwight Yoakam, Little Feat and Vanilla Ice. Nice. Future shows scheduled are Cowboy Mouth, Shooter Jennings, Marty Stuart and .38 Special. (The all-ages Baycenter next door is just about as broad-minded.)
Midnight There is a theory (prevalent mostly among college students) that greasy food helps absorb alcohol. If you're tempted to try the Irish car bomb (Guinness with a shot of Irish whiskey and Bailey's Irish cream) at McShea's Irish Beach Pub & Grill (1705 Route 1; 302-227-9430), side it with the house special bacon cheeseburger and fries or the crab cakes.
7:30 a.m. (Just kidding.) But if you're up and starving, the Sunrise Restaurant is already well into coffee and hash browns (2300 Route 1; 302-227-3202). If coffee and a big, comfy chair sound more soothing, try BookSandCoffee in Ruddertowne (302-226-9959).
8:30 a.m. Dewey Beach is doggie heaven -- one of the few places pets are welcome during the season -- and you can make plenty of two- and four-legged friends just by strolling over to the beach. Bring an old Frisbee, and you're golden as any retriever.
Noon Lunch at Gary's Dewey Beach Cafe Grill (2000 Route 1; 302-227-8519), where the locally famous turkey burger goes for only $6.95.
1 p.m. Dewey Beach is home to the oldest skimboarding competition in the country, so if you're ready to ride the baby waves, get aboard at Dewey Beach Surf and Sport (23 Bellevue St.; 302-227-8288).
3 p.m. Now that you have your feet wet, get a little more extreme with a kiteboarding lesson, a cool $200 from the pros at East of Maui (104 St. Louis St.; 302-227-4703). If you're the observer type, get a free show at the bay access at New Road off Route 1.