Rehoboth Beach for a Winter Escape

Rehoboth Beach at twilight. David Perry photos.
Rehoboth Beach at twilight. David Perry photos.

A Winter Retreat In Rehoboth Beach, Delaware

By David Perry

The plovers skittered across the water’s edge, stopping only to sift a baby crab or worm out of the sand before the next waveWelcome Winter curled in. Minus the local wildlife, it was just me on the beach with all the songs of the sea.

And that was the point: after decking the halls, jiggling the bells, and partying like it was 1999, I really needed a holiday from the holidays.

Rehoboth Beach might be a madhouse in summer, but the winter winds blow away the crowds and shudder the cheesy T-shirt stores, revealing what the town actually is: a sleepy seaside hamlet of stately cedars, quiet streets, and classic clapboard cottages. It’s a post-holiday retreat for the ages.


Driving south from Wilmington’s banks and financial headquarters, I crossed the Roth Bridge at St. Georges and officially entered Lower Delaware. By the time I reached Rehoboth Beach, I was in “Lower Slower Delaware.” If the name doesn’t clue you in, it’s very rural. Locals abbreviate it to “LSD,” and yes, they’ve marketed the hell out of it.

Thrashers in Rehoboth Beach.
Thrashers in Rehoboth Beach.

Rehoboth and I go way back: I’ved summered here since childhood and my grandfather was mayor back in the early 70s; it was his far-thinking that keeps the town the charming beach ‘burb it is.

After a multi-level condo went up on the town’s famous boardwalk — and which casts its shadow on the beach by noon — grandad passed a law to keep all future buildings in town at or below four stories.

This kept the tanning tourists on the beach (and out of the bars) and kept intact the sunny-all-day draw of that same beach, which then and now is the lifeblood of the town. In doing so, militantly quaint Rehoboth spared itself the high-rise hell that swallowed places like Ocean City, MD, whole.

Piping Plovers on the beach in Rehoboth.
Piping Plovers on the beach in Rehoboth.

A Winter Slumberland

I spent the mornings on the boardwalk. Exactly one mile, it is jammed in summer but sees only the occasional jogger in winter. The sea mist moved in overnight, giving the dawn over to shades of gunmetal and lilac, the watery sun no more than a diffuse ghostlight low in the sky. The arcades and fun-rides were in their seasonal hibernation, and I took in the slightly salty breeze on one of the iconic boardwalk benches. Painted a titanium white, they practically glowed in the fog.

As did those plovers. In a bid towards eco-mindedness, Rehoboth planted long stretches of beach grasses at the boardwalk’s edge. It was a case of turning lemons into lemonade; even in the height of summer, no beach-goer ever sets up shop near the boardwalk, but rather gets as close to the water as possible while still avoiding the waves.

Rehoboth Beach.
Rehoboth Beach.

Why not turn this no-man’s land into an animal sanctuary? It was a dazzling success — I never saw plovers, which are endangered, here as a kid. Now scores of them were darting from tuffet to tuffet. For a New Yorker such as myself, any animal that isn’t a rat or a pigeon is downright splendiferous.

Another thing I never saw as a kid were the wave-spotters. Braving the chill, more than a few intrepid souls brought their foldy-chairs to the waves’ edge to watch the Atlantic surge and roil. Perhaps they were into the same decompression-chic I was, or perhaps they were keeping the holiday cheer going; I saw them pass a few bottles and boxes back and forth.

Dogfish Head and Grotto’s

Drag Brunch in Rehoboth Beach.
Drag Brunch in Rehoboth Beach.

I wonder if it was Dogfish Head and Grotto’s; Rehoboth is, after all, where it all started. For such a small town, Rehoboth has an astonishingly outsized headlock on America’s comfort foods:

Once barely known outside its city block, Dogfish is now a national brand; I see it on the shelves in New York. It was just acquired by Boston Beer Company, makers of Samuel Adams Beer.

Not far behind it, Grotto Pizza is all over the tristate.

Both began as holes in the wall I could walk by in a fog, but their multi-building complexes(!) are now so part of the Rehoboth identity that to have beer or pizza someplace else in town is worthy of exile, and packed as much in winter (by locals) as summer (everybody else).

Maybe a little too packed. I wasn’t here to people. It’s why I wandered off The Avenue for Rehoboth’s many cozy “mews,” small alleys daintily lined with shops and cafes that reinforce the Smalltown USA feel; Penny Lane is one of Delaware’s most celebrated pedestrian malls. I curled up at the Coffee Mill on the Rehoboth Mews and had a “gourmet hotdog” — it can be done — at nearby Doggie Style.

Yes, that really is the name, and be prepared for a whole slew of double entendres like that here. Rehoboth is famous as an LGBTQ+ town, which is something else my grandfather started, if unwittingly. While not what the world calls a gay ally, and with no idea his then-yet-to-be-born grandson would be gay, the man was by the book; if it wasn’t illegal, it wasn’t prosecuted.

Consequently, the police were to be hands off if they spotted gay men just kissing or holding hands. In 1971, gays weren’t picky; not being harassed by police for PDAs was as good as got. Word spread. Skip to 2024 and Rehoboth is now the gayest town on the Eastern Seaboard between Fire Island and Ft. Lauderdale, humor included. Butterfly effect, indeed.

Penny Lane, Rehoboth Beach.
Penny Lane, Rehoboth Beach.

And while the resulting gentrification made Rehoboth surprisingly haute (the Cultured Pearl for sushi, Sazio for Coastal Italian, any random house for exorbitant real estate prices), all I wanted was the waves and the plovers. Or a stroll on the very underrated 11-mile Junction & Breakwater Trail, a nature walk linking Rehoboth north through the town of Lewes (“Loowiss”) to the dunes of Cape Henlopen State Park. Hardy hikers can do a round trip in around seven hours, and the pancake-flat terrain makes it easy to focus more on the nature and less on the walk.

I ended my stay as I began it; on the beach, watching the gunmetal waves. No timetables, no to-do lists. Nothing is hard to do, finding a place that is good for nothing — no pun intended — is harder. In a few months, this place would be a beachgoer’s bonanza, but right then, it was a world away. And it’s not every vacation spot when you find something exactly what you were looking for. Well played, Rehoboth.

And good work, Granddad!

Where to Stay

The Boardwalk Plaza on Olive Avenue is one of the best hotels in town, and easily the most themed: it is all about the Victorian Age once you pass the vestibule. It is also right on the boardwalk/beach and just three blocks from Rehoboth Avenue.

David PerryWith work in the BBC and Travelsquire, David Perryhas danced with the dead in Japan, raced across the deserts in Egypt, and gotten into snowball fights with Siberians. That last one is a fool’s game…

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