Delaware is filled with picturesque little towns, and one is known for its historical role in decking America’s halls. According to the Delaware Archives, Milton’s holly history dates back to the early 20th century, when locals started making holiday wreaths from the abundant American holly growing in the area. This blew up into a profitable industry, with wreaths traveling by rail to department stores and homes all along the East Coast. The area around Milton had already earned the nickname “The Land of Holly” by the 1930s, and the town became known as the “Holly Capital of the World,” according to the National Park Service. Not only did its holly industry pump up the local economy, but it also inspired Delaware to adopt American holly as its official tree in 1939.

Nowadays, the commercial holly trade has faded into the background, mainly due to the popularity of artificial wreaths. However, the town still leans into its holly identity. At the Holly Festival in early December, artisans and local vendors take over downtown to sell handmade goods and, of course, celebrate with plenty of holly for the holly-days. For anyone planning a visit, it’s worth timing your trip to witness Milton’s old holly era spring back to life. Wander past well-preserved colonial homes surrounded by quaint little shops in the historic district, then head to the riverside trail known as Governor’s Walk for waterfront views and local history.

Beyond the holiday fun, Milton makes a good basecamp for exploring coastal Delaware, and it’s home to beloved craft brewery Dogfish Head. Plus, being near the East Coast, you can bet your Bethany Big Boys oysters that it has good eats.

For many, Milton shows up on the map for another major reason: Dogfish Head Craft Brewery. Dogfish Head was the first to open a brewpub in the state back in 1995, and it has since grown from the smallest commercial brewery in America to a nationally recognized beer brand. Its main brewery and tasting room are at Cannery Village Center, making Milton a favorite stop for craft beer lovers. This Delaware brewery is a retreat of art, adventure, and imagination — from its iconic Steampunk Treehouse to its focus on “off-centered” beers.

Visitors will find a tasting room and kitchen with more than 40 beer and cocktail taps pouring unique brews, limited-release experiments, and house cocktails made with Dogfish Head’s own spirits. There are rotating drafts and options for growler or crowler fills if you’re taking something back to your rental. Dogfish Head’s tours run year-round and are a fun way to turn Milton into a weekend trip rather than just a quick tasting stop. Walk through the brewhouse and production areas, and learn more about how flagship beers like 60 Minute IPA are made. Some tours include samples and a branded keepsake glass, so it’s worth checking the options and prices online and booking ahead.

The brewery is just a short drive from Milton’s downtown, so you can easily combine it with a walk through the historic district or a meal in town. Hardcore beer fans can round off the experience with a stay in the Dogfish Inn in Lewes (about 20 minutes away).

Interestingly, one of the best restaurants in Milton (according to reviews) borrows influence from further south. Po’ Boys Creole Restaurant serves N’awlins classics like oysters, crawfish, shrimp, and gator bites. Online reviewers say don’t let the humble exterior deter you. This strip-mall dive gets lots of praise for its jambalaya, blackened catfish, gumbo, and crawfish étouffée.

According to Tripadvisor, The Backyard is a favorite for breakfast and lunch. And while the Dogfish Head brewery is best known for craft beers, you can grab a bite too — the menu serves pizzas, sandwiches, and, of course, the classic Bavarian pretzel. However, a short drive (or trolley ride) away in Rehoboth Beach, Dogfish Head’s brewpub Brewings & Eats has a more extensive lineup of wood-fired food, sandwiches, desserts, and more. Reviewers often recommend the “Dogpile” nachos and the pizzas.   

Between meals and brews, you’ve got plenty of options for exploring. Catch a show at the restored Milton Theatre, stroll along the Broadkill River at Milton Memorial Park, or head out to Prime Hook National Wildlife Refuge for some birding and walking trails. And less than 15 minutes away, you can visit Delaware’s only free lavender farm, Lavender Fields at Warrington Manor. While Milton is a bit far from major airports (Salisbury is closest), you can get there in a few hours by bus or take a detour along Delaware Route 1 for a scenic, coastal road trip.