The best bars & nightlife in Sussex County

Tucked inside Plantation Lakes Golf & Country Club but open to everyone, The Landing Bar and Grille nails the sweet spot between relaxed pub vibes and date-night polish, with twelve 65-inch TVs, a sunny patio, and a legit lunch-and-dinner lineup including gluten-free and vegetarian options.

From the Millsboro newsletter, October 14, 2026

Whether you're mead-curious or full-on horn-raising, Brimming Horn Meadery / Bear Cult Brewing- Seaford pours award-winning meads alongside fruit wines, ciders, and their own Bear Cult beers, making it an easy local move when you want something bolder than the usual grocery-store sixer.

From the Laurel newsletter, October 22, 2026

Twin Branch Winery brings a mellow Milton backdrop, thoughtful from-vine-to-bottle pours, and a calendar of live music that makes lingering easy. Grab a sampler to explore everything from TBW Chardonnay to the King Cole red blend, or rope the crew into a low-stress party and call it a day.

From the Georgetown newsletter, September 30, 2026

A Seaford standby since 1987, Cinnamon’s CC 22 serves classic American plates and Chef Tracey Hastings’ occasional curveballs, all with that Delmarva-seasonal touch locals know and love. It’s the kind of spot where old friends turn into family, good bites meet cold drinks, and weeknights suddenly run long.

From the Laurel newsletter, October 6, 2026

The Listening Booth is a nonprofit venue built for connection through original music, songwriting, and storytelling, with intimate concerts, open mics, and Sunday jam nights. They also teach, offering private lessons and group classes with working musicians, so you can listen, learn, and maybe accidentally form a band.

From the Lewes newsletter, October 2, 2026

Blue Heron Grille keeps it simple and tasty with fresh salads, grilled sandwiches, and healthy wraps that hit the spot whether you played 18 or just popped in. They also cater golf tournaments and special events, so keep them in mind when the team needs an easy win.

From the Milton newsletter, October 2, 2026

Revelation Craft Brewing keeps Georgetown well hydrated with award-winning beers, a taproom that leans local, and a creative streak that never sits still, from new beer releases to community events.

From the Georgetown newsletter, October 19, 2026

The Atomic is the kind of neighborhood hang for legit smoked pub fare, from deviled eggs and chorizo-queso nachos to brisket quesadillas and double smash burgers.

From the Laurel newsletter, October 14, 2026

Lewes Brewing Company sits along the Lewes-to-Georgetown Trail pouring a fresh tap list, including Mr. 5% rice lager with Sorachi Ace hops. Check their menu and events, then swing by for an after-work pint with neighbors.

From the Lewes newsletter, October 21, 2026

Whether you’re chasing a new Tasting Room Exclusive or just want the freshest off-centered ales, Dogfish Head Milton Brewery keeps 40+ beer and cocktail taps flowing, with growler and crowler fills to go. Spot the Steampunk Treehouse, grab pizza or a wrap, then hop on a daily tour.

From the Milton newsletter, October 13, 2026

If you want that beach-town taste of the Irish without leaving Milton, Irish Eyes Pub & Restaurant nails the mix of hearty pub fare, great times, and live entertainment. Easy spot to catch up, mark a birthday, or just linger over another round while someone else handles dinner.

From the Milton newsletter, September 27, 2026

When you want to watch the big game without arguing over the remote, RnR Sports Bar has plenty of screens and a few pool tables to keep the crew happy. Menu leans hearty, think wings, loaded nachos, Maryland Crab Soup and a solid ribeye, plus straightforward drinks that don’t overcomplicate things.

From the Seaford newsletter, October 14, 2026

Delaware’s first and only award-winning winery, Nassau Valley Vineyards-Winery offers relaxed tastings, laid-back tours, and a wine shop for easy restocks, plus a charming farmers’ market and rental-ready spaces when you need them... all one quick turn off the highway and blissfully quiet.

From the Georgetown newsletter, September 27, 2026

Vino Del Mar is the wine-forward hangout built around community, with chef-crafted small plates, crisp flatbreads, and thoughtful charcuterie lining up beside a smart list of wines, balanced cocktails, local beers, and zero-proof picks.

From the Lewes newsletter, October 15, 2026

The Benjamin keeps Seaford evenings classy with innovative cocktails, endless whiskey options, and a tidy roster of wines and craft beers. Expect rotating local food trucks like Cousins Maine Lobster and Smash Mouth, plus happy hour, trivia, and game nights that turn just one drink into a full evening.

From the Laurel newsletter, October 17, 2026

Salted Vines Vineyard & Winery keeps things lively with daily signature tastings, take-home glasses, and a steady lineup of live music and food trucks. If you like your local nights mellow but still social, their concert series and events calendar make it an easy go-to.

From the Berlin newsletter, October 6, 2026