History, Arts & Culture Itinerary: An Epicurean’s Dream Weekend Getaway

A trip to Kent County is sure to tantalize your taste buds and delight your inner history buff. With Delaware’s best wineries, breweries and unique distilleries throughout the villages, dozens of museums and historical sites

including three stops on the Harriet Tubman Underground Railroad Byway — and luxurious accommodations at Dover Downs Hotel & Casino, Kent County is the perfect place to immerse yourself in a long weekend full of flavors, fun and a host of activities to satisfy any appetite!

Please be sure to confirm hours of operation for all restaurants and attractions to ensure they’re open before you head out. Some operate within limited hours and by appointment only.

Day 1: Dover

The 300-Year-Old Capital City of Delaware is Home to Historical Sites, Charming Museums and More

Start your day with a hearty breakfast at The Countrie Eatery, then immerse yourself in the history of the First State with a visit to the Delaware Agricultural Museum & Village for a memorable and educational blast from  the past on what life in rural Delaware was like. Once you’ve had your fill of historical farm life, head to the historic Christ Episcopal Church at First State Heritage Park.  This church, founded in 1703, is listed on the National Register of Historic Sites and contains a beautiful old cemetery.

Take the rest of your afternoon to discover all that First State Heritage Park has to offer! The park features historical sites, walking tours, quaint country stores and more. You won’t want to miss these attractions, including:

While at First State Heritage Park, be sure to visit Governor’s Café for lunch. This local treasure is housed in the historic Leason House built in 1857 and is directly across the street from the Woodburn Mansion. Before you leave the area, also check out Kent County Courthouse Courtroom One for a fascinating journey through the history of Delaware’s judicial system and stories of the judges that have sat behind the bench throughout the years. Ready to relax? Enjoy a fun, traditional pub dinner at McGlynns Pub & Restaurant before heading back to the hotel to rest up for day two!

Day 2: Explore Dover & Smyrna

A Full Day of Good Eats and Gripping Historical Sites You Don’t Want To Miss

Get started early with breakfast right inside the hotel at the Festival Buffet! Then begin your day by discovering Delaware’s long, storied military history. Celebrate and remember those who fought bravely in the Vietnam War with a visit to the Kent County Veterans Memorial Park, established in 2009 by the Vietnam Veterans of America and the Kent County Levy Court. Then head out to the Air Mobility Command Museum by Dover Air Force Base to experience our nation’s aviation history and see over 30 incredible aircraft, including Air Force Two, the aircraft that flew past vice presidents.

From there, head out to the John Dickinson Plantation, the ancestral home of John Dickinson, one of the founding fathers of the United States, signer of the U.S. Constitution and “Penman of the Revolution.” Then head over to the town of Smyrna to continue your tour of 18th-century life with a visit to Historic Belmont Hall, built in 1773 by Thomas Collins, a Delaware politician during the American Revolution.

Day 2: Explore Dover & Smyrna (continued)

Ready for lunch? Check out Brick Works Brewing & Eats and enjoy burgers and beers made fresh with locally sourced ingredients. Keep the good times flowing with a visit to Painted Stave Distilling, Smyrna’s local craft distillery, for a tour and tasting. Take time to visit another stop on the Harriet Tubman Underground Railroad Byway at Blackbird State Forest, one of the last stops before the final passage to freedom for the extraordinary, brave people who made this journey.

Enjoy happy hour at Blue Earl Brewing, Delaware’s seventh microbrewery, before leaving Smyrna. As you head back towards Dover, swing by the Star Hill Museum/ AME Church (just south of Dover) for one last dive into history for the day. This 19th-century church was home to a large population of freed slaves, and members are believed to have participated in guiding the Underground Railroad through the region.

Devour a delicious dinner at one of the two restaurants owned by the Forbes family, Cool Springs Fish Bar and Restaurant or Restaurant 55 — either is a great choice, depending on what you might be craving! Relax, refuel and get ready for day three.

Day 3: Explore Camden, Marydel, Milford & Frederica

A Lazy Morning Leading to a Day of Libations

Grab a late breakfast at Diamond State Grill and be sure to eat up — you’ve got a long day of tastings ahead of you!

Make your first stop at Fordham & Dominion Brewing Company and enjoy a craft beer tasting in a rustic tap room. From Dover, head into Camden — drive past the Camden Friends Meeting meetinghouse for a peek at this abolitionist landmark, as well as the final Kent County stop on Harriet Tubman’s Underground Railroad Byway at Willow Grove in the Norman G.Wilder Wildlife Area. Then you’re off to Marydel to Harvest Ridge Winery to savor wines from this family winery nestled in the beautiful Delaware countryside.

Venture over to Milford and take a leisurely stroll through Abbott’s Mill Nature Center. Then head over to the Milford Museum for a charming snapshot of this town’s nearly 300-year-old history.

Keep the buzz going with your next stop at easySpeak Spirits with a variety of handcrafted cocktails and tasting plates, then compliment your meal with a sample (or two) at Mispillion River Brewing. Reserve a private tour for a  closer look at this cool, laidback brewery.

Take a walk through the Milford Art Stroll  while you digest and enjoy the beauty and charm this town has to offer! Then head on over to Frederica to see the famed Barratt’s Chapel & Museum, known as “The Cradle of American Methodism.” Wrap up your day with a visit to the nearby Bowers Beach and the Bowers Beach Maritime Museum and discover the history of this area of the Delaware Bay.

End the day with dinner at a Delaware destination, J.P.’s Wharf Restaurant and Bar. This local favorite specializes in seafood and has a relaxing, enjoyable location on the water. Savor your last evening in Delaware’s Quaint Villages over fresh oysters, fish, blue crabs and more.

Day 4: Felton & Harrington 

Take time on your last day to fully enjoy Dover Downs Hotel & Casino as long as you can! Enjoy brunch at Michele’s and then, when you’re ready, head to Pizzadili Vineyard & Winery for a final delectable tasting. Wrap up your tour of Delaware’s Quaint Villages with a stop in Harrington and visit its quaint local museums, including the Greater Harrington Historical Society Museum and  the Harrington Railroad Museum. Be sure to stop in at the Messick Agricultural Museum as well for exhibits featuring antique farming machinery, automobiles, tools, toys and more memorabilia.

There’s always more to see in Delaware’s Quaint Villages. This trip is just a taste — and we have a feeling that before long, you’ll be planning your next trip, ready for more!

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