Top 10 Weekend Trips In Delaware, USA

weekend getaways from delaware
Swadeep Singh
Swadeep Singh 
| 4 min read

Delaware was the first state to be admitted into the union, and thus it is known as the foundation stone of United States of America. It is also the second smallest of all the states, yet its tourism diversity is amazingly greater than many larger states. As we all are aware of the fact that it took the name from Delaware river and bay, the tourism scenario is not limited to just these two elements. Delaware showcases a splendid coastline, heritage places, state parks, shipyards, breweries, and more. Then, there is also the iconic cuisine that is associated with just this state. Owing to the tiny size, it is easy to be explored entirely and if you’re also planning for a visit to the ‘First State’ anytime soon, you might want to have a look at our recommended weekend trips in Delaware.

1. Millsboro

Harmon School 1 Millsboro Sussex Co DE
Source: Photo by Wikimedia Commons user Smallbones used under CC0

This family-friendly little town, offers beautiful scenery, rich tribal history, and old city charms. Being situated on the banks of Indian River, Millsboro is surrounded by several wetlands and natural areas; the notable ones are Betts Pond, Millsboro Pond, and Trap Pond State Park. Owning to Nanticoke Indian Museum that is located within the town, you get the opportunity to learn the background of an indigenous tribe. Plus, you should also visit the splendid Mary Mother of Peace Catholic Church, and Delaware’s last remaining single-screen movie hall, Clayton Theatre. Cupola Park and Antique Mall of Millsboro are also worth visiting.

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2. Fenwick Island

Fenwick Island Lighthouse
Source: Photo by Wikimedia Commons user Delfi4110 used under CC BY 3.0

This is a resort town located approximately 19 miles (30 kilometers) far from Millsboro. Fenwick Island sits in the middle of a long barrier stretch that is situated between Little Assawoman Bay and the Atlantic. Although pristine beaches are the specialty of this wide sand bar, the distinction of Fenwick Island is with its serenity; the place is really quieter than nearby beach towns. If you’re visiting Fenwick Island, you should check Discoversea Shipwreck Museum, Fenwick Island Lighthouse, Assawoman Wildlife Area, and Nicks Mini Golf.

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3. Rehoboth Beach

Rehoboth Beach, Delaware
Source: Photo by Wikimedia Commons user Patrick Nouhaille... used under CC BY-SA 3.0

This beach town was founded in 1873, but you can find the building even more historic than that of the English and Dutch have already settled here in the mid-17th century. Rehoboth Beach is situated a few miles north to Fenwick Island, just before the starting point of the barrier beach. It is known as the most visited resort town in the state, and besides the most evident tourist attractions like the beach and the boardwalk, there is still a lot to do here. Look into the town’s history at the beach museum, and do visit the Beach Bandstand as they usually hold free concerts in the evenings.

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4. Milton

Milton Delaware
Source: Photo by Wikimedia Commons user w:Malepheasant used under CC BY-SA 2.5

Milton is located approximately 15 miles (24 kilometers) from our previous location, Rehoboth Beach. Being another really small town in Delaware, it was settled in the 19th century specifically for shipbuilding purposes. But Milton didn’t thrive well until the end of the Civil War, at which point, it was taken into consideration by the distilleries as well. Today, it is a prime tourism destination for those who would like to take brewery tours and tastings. Besides, people may also visit the natural preserves like Prime Hook National Wildlife Preserve and Broadkill River. The bay is also a couple of miles to its east.

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5. Newark

Newark DE Main Street
Source: Photo by Wikimedia Commons user PookieFugglestein used under CC0

Newark is the third-largest city in the state of Delaware that is located to its extreme north and comes midway between the two great metropolitans, Philadelphia and Baltimore. Newark shows a great opportunity for park and recreation, as this little city covers at least 34 parks and over 10 lakes. Moreover, it’s the home to the University of Delaware, which is apparently the most happening place in the city. The campus features many sporting arenas, an ice rink, music theaters, and galleries.

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6. Lewes

Lewes Delaware
Source: Photo by Wikimedia Commons user w:Malepheasant used under CC BY-SA 2.5

Lewes is a tiny town in Delaware that is located at the mouth of its bay. Founded in the year 1631, you can obviously tell that Lewes has a rich heritage and stories to tell. Thankfully, the tourists can cover this entire city on foot as it is merely 4.72 sq mi (12.24 sqm) wide. Besides, Lewes boasts extensive beach stretch and an old town aura. Further, it is bordered with two vast conservation areas, namely - Great Marsh Preserve and Cape Henlopen State Park. Both of which are famous for bird-watching, canoeing, and hiking tours.

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7. Delaware City

Del City Hotel DE
Source: Photo by Wikimedia Commons user Smallbones used under CC0

Delaware City is a tiny population located at approximately 20 miles (32 kilometers) south of the most populous city of this state, Wilmington. Being a really small place, Delaware has a big name in tourism already; it has a rich architectural heritage and flawlessly planned uptown. The city houses over 250 historic structures. The notables are within the former military base of Fort DuPont State Park and Fort Delaware State Park. If your visit is short, make sure to explore the entire 322 acres (130 hectares) of Fort DuPont, as it celebrates all the good events of the year.

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8. Smyrna

Main Street NB approaching Commerce Street Smyrna DE
Source: Photo by Wikimedia Commons user Dough4872 used under CC BY-SA 4.0

The town of Smyrna is situated in the heart of Delaware, at nearly 14 miles (22 kilometers) down from the most populous city of the state, Wilmington. Just like Milton, this town was also established for shipbuilding but people have developed it instead into their preferred residential near Wilmington. You would definitely like to spend a relaxing family weekend trip in this peace-loving settlement. To have something to do here while enjoying this short visit, it will be a good idea to hike at Blackbird State Forest. You may also visit Smyrna Museum and learn the town’s history since the times of the Civil War.

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9. Bethany Beach

Bethany Beach - panoramio (10)
Source: Photo by Wikimedia Commons user Doug Olson used under CC BY-SA 3.0

Bethany Beach sits in the middle of the route between Fenwick Island and Rehoboth Beach. You can enjoy tax-free shopping, lazy beach aura, and boardwalk entertainment here. This is the perfect place to spoil yourself and have a great time with friends or family.

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10. Dover

Source: Photo by Wikimedia Commons user JERRYE & ROY ... used under CC BY-SA 3.0

Dover was founded as a court town in 1683, which was then converted to a city just after a couple of decades. Official commissioning authorized Dover to gain the capital status of Delaware in the same century, and it is still serving as the state’s capital. Dover holds such a rich heritage and harbors so many museums. Air Mobility and Command, John Victrola, Biggs, State Police, and Agriculture Museums are the names of the few notable ones. Besides, Dover is world-renowned for its NASCAR venue and Firefly Music Festival.

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Good things come in small packages

Wilmington Delaware skyline
Source: Photo by Wikimedia Commons user Malepheasant used under CC BY-SA 2.5

Although we understand that Delaware is a relatively smaller state, you cannot deny the fact that it is equally amazing as any larger state. It boasts a beautiful bay, barrier islands, state parks, marshes, historic districts, and more wonders. Hopefully, this list will help you develop an awesome itinerary of this little state.

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Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.


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Also known as Bobby, Swadeep Singh is a businessman since 2013 but he has forever nurtured a passion for writing. Traveling never makes him exhausted, which is why he's never known turn down any...Read more

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