6 Romantic Small Towns In Delaware For A 3-Day Weekend

For couples looking to make the most of a long weekend, Delaware has plenty of romantic towns. Located along the Atlantic Ocean, the state is known for its beautiful beaches and inviting boardwalks where visitors can relax, enjoy nostalgic arcade games, and indulge in classic treats like taffy and corn dogs. Plus, there are numerous dreamy vintage inns and bed-and-breakfasts to choose from in top towns like Lewes and Rehoboth Beach. Find out for yourself how lounging oceanside or exploring history can be intimate in these six romantic small towns in Delaware for a three-day weekend.

Rehoboth Beach

The Rehoboth Beach Boardwalk has everything needed for a date without traveling far. Bask in the sunshine, grab dinner and drinks at a local favorite spot, and listen to or watch the live entertainment that can all be found on the mile-long boardwalk running along the beach. Unleash your inner child at Zelky's Beach Arcade before dining at Chesapeake & Maine, then taking in some live music at the boardwalk bandstand. For a more secluded activity, stroll along the bay shoreline at Delaware Seashore State Park. Explore the state's history, paddleboard in the bay, or try your hand at fishing in this epicenter for outdoor recreation. Take one of the park's trails, or relive history at the Indian River Life-Saving Station. Built in 1876, the station was used to house surfmen who patrolled the coast, and today it is a museum honoring their service as well as local maritime culture.

Enjoy a luxury weekend stay at The Bellmoor Inn & Spa. Located in the lively beach town of Rehoboth Beach but removed from the center of the action, the inn is perfectly situated for a serene visit. Stay in one of its historic rooms, relax by the pool, or book a soothing spa day.

Lewes

Cape Henlopen State Park in Lewes is famous for its 5,000 acres of natural wonder, including captivating beaches, maritime forests, diverse habitats, plentiful wildlife, and so much more. Spend the day roaming the paved paths or walking along the shoreline of the Atlantic Ocean and Delaware Bay beaches. For more whimsy, the Historic Lewes Farmers Market offers visitors jams and jellies, specialty-cut flowers and herbs, goat milk skin care, local fresh produce, small batch coffee, blue crab, and even more. Featuring local and regional vendors, the market has everything you might need for an enjoyable oceanside weekend.

Grab some items and check in for a stay at Dogfish Inn. Using the same quality and craft in their rooms as in their beer, the inn is a base camp for beer lovers and outdoor enthusiasts. Conveniently located near a kayak and boat launch, a snaking bike trail, and scenic beaches, guests can enjoy the luxuries of the day and, at night, cozy up around the fire pit before retreating to one of the retro rooms.

Bethany Beach

Soak in the views and stay for a stunning sunset at the Bethany Beach Boardwalk. The boardwalk offers a quaint, traditional beach town experience as well as shopping, dining, and live entertainment. Ice cream, pizza, and Italian sandwiches are just a few of the favorite foods available on the boardwalk, while exceptional boutiques, gift shops, and a bandstand give visitors more opportunities for fun. For even more great food and live music, enjoy a dinner at Bethany Boathouse. The open-air restaurant has been serving patrons since 2015 and hosting local musicians, energetic bands, and trivia nights.

Great times, great food, and a great sleep are all part of an ideal getaway. So, book a stay at Bethany Beach Ocean Suites Residence Inn. The oceanfront hotel provides unmatched views of the sunset over the waters nightly, for guests to enjoy from their private balcony. The indoor/outdoor saltwater pool is located on the rooftop, letting guests soak, relax, and take in the view.

New Castle

Appreciate history, architecture, solitude, and tranquility in New Castle by strolling through Delaware's first court and state capital at the New Castle Court House Museum. Built in 1732, the structure is one of the oldest surviving courthouses in the United States, as well as a National Historic Landmark. Appreciate not only the significance of the building itself but the story it holds inside. Learn about one heroic family's journey to freedom on the Underground Railroad, and the impact Swedish, Dutch, and English settlements had on the culture and social developments of New Castle through the exhibits on display. For another unique attraction, explore the beauty of Read House & Gardens. From the roof, guests can view the Delaware Memorial Bridge, Delaware City, New Jersey, and a power generation station, all located along the Delaware River. The colonial-revival house itself holds unmatched beauty in its 14,000 square feet, which has been featured in Town & Country and Mademoiselle.

After a visit to the home built for George Read II and his family, spend the night in another lovely home at the Terry House Boutique Hotel. Each room is adorned with its own character and charm for a personalized experience. Purchased as a family residence in 1851, the building has had many owners but still retains its original charm. Each of the seven unique rooms has its own theme and catchy name. Pretty In Pink and Enchanted Gardens are just two of the rooms to choose from, while guests can also gather in the parlor, patio, or kitchen.

Milford

Dive right in to Milford and explore the charm and calm of this small river town. Stroll hand in hand along the Mispillion River on the Mispillion Riverwalk. The mile-long stretch of path along the river weaves through the heart of downtown, allowing for stops along the way. Once a year, the riverwalk hosts the ever-popular Milford Riverwalk "Freedom" Festival, which is the town's largest outdoor festival. Experience more nature involving the Mispillion River at the DuPont Nature Center. Located where the Mispillion River and Cedar Creek meet at the Delaware Bay, the center provides extensive coastal views. The observation deck at the center is recognized as one of the top East Coast spots for observing spring shorebird migration.

For a magical weekend, book a stay at The Towers Bed & Breakfast. Once home to the state's most famous poet, as well as a Delaware governor during the Civil War, the inn has seen its fair share of history. Built in 1783 and remodeled in 1891 to the Steamboat Gothic style it is today, The Towers provides an alluring trip back in time for overnight guests. For couples checking in, the inn also offers a romance package providing a floral arrangement and sparkling wine.

Dover

Enjoy a diverse historical attraction in Delaware's first urban park without boundaries. First State Heritage Park shares the stories of remarkable figures in the state's timeline and is made up of multiple partner sites. Centered around historic Dover Green, the park includes the John Bell House Interpretive Center and Legislative Hall, along with the exterior sites of the Biggs Museum of Art, Woodburn (the governor's residence), and the Johnson Victrola Museum (temporarily closed until fall 2026). After a historically charged afternoon, mingle in the local beer garden at Rail Haus. Enjoy a beer, cocktail, or meal while lounging in downtown Dover, or check out their events calendar and make a night of it with live music or trivia.

For the evening, check in at the State Street Inn. Just a short walk from restaurants, museums, and historic sites, guests can enjoy all their amenities and then stroll into the heart of Dover for a night out. Cozy up in the living room with a fireplace, soak in the sun from the reading room, enjoy morning coffee on the front porch, and take in the beauty of tree-lined State Street.

There is no doubt that Delaware is filled with history, being the first state in the union, and that history can be found in the Victorian buildings, nationally recognized forts, and local parks. Each legendary landmark has its own unique story, significance, and beauty, making this state a truly memorable destination. Spend the day beachside in this coastal state and end the night cuddled up in a vintage bed and breakfast. Stroll through historic gardens, enjoy a couple's massage, or simply take in the charm of these six romantic small towns in Delaware for a three-day weekend.