7 Ideal Delaware Destinations for a 3-Day Weekend in 2025

A standard two-day weekend often feels too short to fully enjoy an out-of-town getaway. Just as you start to unwind, it's already time to pack up and return home. That’s why a three-day weekend presents the perfect opportunity to make the most of your time off, allowing for deeper relaxation or adventure without feeling rushed. If you're planning a trip for an upcoming long weekend—whether to unwind in tranquility or embark on an exciting exploration—Delaware is an ideal destination. Overflowing with hidden treasures, the state boasts a diverse mix of lively coastal towns, captivating historical sites, and exceptional local dining, along with a wealth of outdoor activities that cater to all ages.

Milton

Discovered in the coastal Sussex County of the state, this warm community is home to a wide array of unique attractions that accommodate the interests of personalities and ages of all types, making it an ideal destination for a quick escape from urban life. Millsboro's founders were European settlers of English descent, primarily second-generation colonists who migrated north from Virginia's Eastern Shore. Drawn by the timber boom of the late 17th century, they arrived in search of opportunities to harvest the region's extensive mixed deciduous forests. Notable landmarks like the Milton Historical Society & Lydia B. Cannon Museum stand as a genuine treat for history buffs. The Society gathers, safeguards, and shares stories, artifacts, and documents connected to Milton and the Broadkill Hundred, aiming to support study and education through its exhibitions, such as Two Centuries of Milton. For pristine outdoor experiences, the town jewel, the Broadkill River, wields an abundance of activities from fishing along the riverbanks, birdwatching, kayaking, and canoeing, complemented by its beautiful surroundings. Other local staples include the 18th-century constructed house of Governor James Carey, Delaware’s governor, a site for those interested in the town's history.

After a long day of exploration, the Dogfish Head Craft Brewery is an ideal place to unwind, accredited to its innovative brewing techniques and a tasting room where visitors can sample a variety of creative beers that guarantee great conversations and memorable experiences, especially for beer aficionados. Residing at the heart of the town is the Milton Theatre, a venue dating back to the early 20th century, which currently serves as a hub for live entertainment, from plays and musical performances to movie screenings. This small town is a must-see that will satisfy the needs of diverse crowds, attracting retirees from major East Coast cities, along with numerous young and middle-aged families with longstanding ties to Sussex County.

Millsboro

Millsboro is an excellent destination for a three-day weekend, offering a great mixture of natural beauty, rich history, and charming local attractions. Nature enthusiasts can explore Cupola Park, a scenic riverside spot perfect for picnicking, fishing, or relaxing by the water. The park offers top-tier views of the Indian River, creating a peaceful escape for visitors seeking a few days of harmony. For those who love the outdoors, a visit to Trap Pond State Park, just a short drive away, is a must. Here, you can kayak or canoe through the cypress swamps, walk along mesmerizing hiking trails, or simply enjoy the unforgettable surroundings of this natural gem.

History buffs and cultural enthusiasts will enjoy the Nanticoke Indian Museum, which offers an immersive experience of the history and traditions of the Nanticoke people through fascinating artifacts and exhibits. The Museum additionally includes lessons in cultural arts and crafts, native drum and dance programs, educational initiatives, heritage and cultural activities, programs for youth and seniors, elder support services, healthcare offerings, and mental health and domestic violence support services. To dive deeper into the town’s heritage, the Millsboro Historical Society displays the area’s evolution and its connection to the timber and maritime industries of the past. For a taste of varying flavors and shopping options, stop by the charming Antique Alley of Bridgeville for unique finds and vintage treasures. Millsboro fuses natural grandeur with cultural depth, making it an ideal spot for a well-rounded weekend getaway.

Lewes

The first town in the state of Delaware is a secluded wonder, perfect for anyone seeking a calming and blissful weekend. To start your weekend, head to the Zwaanendael Museum to delve into Lewes' maritime history. Built in 1931 to commemorate the 300th anniversary of the first European settlement in Delaware, this museum is modeled after a Dutch City Hall. The museum's exhibits showcase the history of Sussex County by highlighting the lives of those who inhabited Delaware's southeastern coast. Featured displays cover local history, shipwrecks, lighthouses, the Cape Henlopen Lighthouse, the British bombardment of Lewes during the War of 1812, Delaware River and Bay pilots, and the dynamic changes of the Delaware coastline over time. For more excitement, the floating museum known as the Lightship Overfalls is one of just 17 surviving lightships out of the 179 constructed between 1820 and 1952. Recognized as a National Historic Landmark in 2011, it is one of seven lightships in the United States still accessible to the public. With the lightship as its focal point, the Overfalls Foundation is dedicated to preserving, showcasing, and educating others about the maritime history of Lewes, Delaware Bay, and the surrounding coastal region.

New Castle

Just ten minutes from downtown Wilmington, New Castle is a charming community that embodies the essence of small-town life. Unveiled along the Delaware River, it boasts a prime location surrounded by some of the most breathtaking scenery in the area. History fanatics will appreciate landmarks like the New Castle Court House Museum, one of the oldest courthouses still standing in the United States. The town is also home to the Dutch House, believed to be one of Delaware’s oldest surviving residences. Built in 1732, this courthouse played a significant role in Delaware's history. It was the site where Delaware declared its independence from Pennsylvania and England in 1776. Meanwhile, the New Castle Farmers Market offers a vibrant and lively shopping experience that feels far from small. Thanks to dedicated preservation efforts, New Castle maintains its historic allure, contributing to its charm for the nearly 5,549 residents who call it home. Despite being close to Delaware’s more urban areas, New Castle preserves its peaceful and warm character through its interesting history and community-focused atmosphere.

Delaware City

Delaware City, located in New Castle County, is an inviting port town positioned on the eastern side of the Chesapeake and Delaware Canal. Its strategic location provides access to the Delaware River to the east and the Chesapeake Bay to the west, making it a vital connection point for waterway travel and commerce. What makes this town a perfect spot for a weekend escape is its dynamic combination of cultural, commercial, and natural highlights. To start off, the Fort DuPont State Park, a preserved plot of land situated at the mouth of the C&D Canal, is filled with recreational activities, including fishing, biking, horseback riding, disk golf, hunting, boat launches, and hiking. The Park also provides youth engagement programs, such as scouting clubs, summer camps, and school-based initiatives. For a taste of regional history, wander over to the Delaware City Historic District and soak in the delights of 19th-century architecture. It’s perfect for a self-guided walking tour to explore historic homes, storefronts, and landmarks.

Pea Patch Island, located at the core of the Delaware River, is a classical marvel where the iconic Fort Delaware was originally constructed in the mid-1800s. Today, visitors can explore this impressive fortress, including key areas like the barracks and parade ground, which showcase its rich past. The island is also a haven for birdwatchers, offering trails and an observation tower that provides opportunities to spot nine distinct species of ibises and herons. For those planning a three-day weekend to experience the island's unique blend of history and nature, access is exclusively available via ferry, ensuring a memorable and soothing journey.

Odessa

Odessa is an enchanting destination for those with a passion for history. As one of Delaware’s oldest towns, it traces its origins back to the 1660s when Dutch settlers first established a community along the Appoquinimink River. Later taken over by the English, Odessa flourished into a bustling port town, a legacy that is still evident in its well-preserved colonial and Federal-style architecture. Today, this charming town offers a picturesque escape, with beautifully restored historic homes, tree-lined streets, and cute cafés that make it perfect for a relaxed afternoon of discovery.

A highlight of any visit is a tour with the Historic Odessa Foundation, which treats excursionists with an enriching look into the town’s layered past. Wander through meticulously maintained gardens and period-accurate buildings, including the Corbit-Sharp House, a National Historic Landmark that played a hefty role in the Underground Railroad. Other must-see landmarks include the Old Academy, which once served as a schoolhouse in the 18th century, and the Collins-Sharp House, a rare example of early Delaware architecture that offers insight into daily life in the 1700s. Visitors can also explore the Old Bank, a beautifully preserved 19th-century structure that reflects the town’s commercial history, and the historic Pump House, a key element of Odessa’s early infrastructure. Beyond its rich history, Odessa hosts engaging annual events, including the Historic Odessa Brewfest in early September. This lively festival brings together craft beer enthusiasts, live music, and an abundance of vendors, offering a fantastic way to experience the town’s welcoming community.

Newark

Newark prospers with a youthful aura thanks to its eclectic college town energy, anchored by the historic University of Delaware, one of the nation’s oldest institutions, founded in 1743. A stroll through the campus grants visitors a chance to soak in its history and beautiful surroundings. The campus blends stunning Georgian-style architecture with modern facilities, creating a perfect harmony of past and present, while highlights like the Old College Hall, home to an art museum and historical displays, make it a legacy piece. Additionally, don’t miss the University of Delaware Botanic Gardens, a hidden gem featuring diverse plant collections and placid year-round gardens, open to the public at no cost. It’s the perfect spot for a peaceful walk or an educational outing, illustrating the university’s commitment to environmental stewardship. Adjacent to the gardens, treat yourself to a sweet experience at the UDairy Creamery, a student-run enterprise that retains over 34 flavors of ice cream. Each scoop is crafted on-site using milk sourced directly from the university’s Agriculture College dairy farm. Supporting the creamery not only satisfies your taste buds but also helps fund hands-on learning opportunities for students.