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6 Picturesque Small Towns in Delaware for a Weekend Retreat

by Staff

Delaware is one of the smallest states by land area in the United States. With only 100 miles long and no more than 30 miles wide, it has a surprising historical profile of being one of the Thirteen Colonies that took part during the American Revolution and was the earliest state to ratify the country’s constitution in 1787, hence earning its nickname “The First State.” Fast forward to today, Delaware is known as an onshore corporate haven for many publicly traded companies in America. At the same time, visitors are drawn to its beaches and festivals in the summer months, as well as its number of quaint small towns that offer a nice getaway for as quick as a weekend. From its rural heartland to the coast, here are six picturesque small towns in Delaware for a weekend retreat. 

New Castle

Historical town of New Castle, Delaware.

Less than 10 minutes of drive from downtown Wilmington, depending on traffic, is the riverside community of New Castle. It is the oldest continuously inhabited town in the Delaware Valley, with a founding history dating as early as the 1650s. Some of its earliest structures are seen in the First State National Historic Park; for the town, it includes the Court House, which has become a museum highlighting the events that happened in the area.

Explore the historic core where the Amstel House and Read House and Gardens are located before a relaxing stroll along the shoreline of Battery Park. When it is time for a meal, Jessop’s Tavern delivers the best pub-style dishes and a staggering selection of 30 types of local draft. Stay for a night or two at Terry House, a bed-and-breakfast in a brick townhouse with a lovely garden right in the heart of downtown. 

Smyrna 

Northbound view of Main Street approaching the intersection with Commerce Street in Smyrna, Delaware, USA.
Northbound view of Main Street in Smyrna, Delaware, USA. By Dough4872, CC BY-SA 4.0, Wikimedia Commons

A little north of the state capital, Dover, the town of Smyrna, is noted for its art scene. The Smyrna Opera House is perhaps the best representative of that, operating since the late 19th century; it is the main venue for live theater performances and events while also having an art gallery of its own. Follow along Main Street to take in the architecture of its registered heritage buildings and visit the Smyrna Museum before delving into the local eateries such as Brick Works. One should also consider joining a tour at Painted Stave Distilling to learn about the process of making the town’s best-known craft spirit.

Close to town, the Bombay Hook National Wildlife Refuge has excellent birdwatching on its trails and observation decks. A day of activities can be tiring; spend the evening relaxing in the pool or have a much-needed rest at Quality Inn, a preferred choice for most visitors here. 

Milford

View at the beginning of the walk on the Milford, Delaware River park walkway.
View at the beginning of the walk on the Milford, Delaware River Park walkway. Editorial credit: Don Garrard / Shutterstock.com

Milford lies in the center of the state, grown from a shipbuilding industry on the Mispillon River. Since its turn as a commercial hub for the agricultural community of Delaware’s south in the mid-20th century, the town slowly reformed into what it is today, with locally owned boutiques, art galleries, and restaurants scattering across its perimeter. Milford promotes its historical roots through the exhibits of its namesake museum, as well as on the Mispillon Riverwalk, where visitors can jog, bike, or stroll along the waterway.

The same site also hosts the Riverwalk Freedom Festival every September 11th, an exciting outdoor event not to be missed. The leafy setting of Milford makes it a desirable place for a retreat, with a wide range of bed-and-breakfasts such as The Towers and Causey Mansion, both of which are conveniently in the center of town. Of course, if you are after spacious rooms and a swimming pool, the Comfort Inn will suit your requirements. 

Lewes

Aerial view of Lewes, Delaware, showcasing the beach town, fishing port, and waterfront residential homes along the canal.
Aerial view of Lewes, Delaware. Editorial credit: Khairil Azhar Junos / Shutterstock.com

“The First Town in The First State” is what Lewes holds firmly to its identity; founded in 1631, it was the first established European settlement in Delaware. With a walkable downtown, visitors have a breeze exploring the historic district where several museums, such as the Main Campus of the Lewes Historical Society and the Zwaanendael Museum, as well as the restored Lightship Overfalls, are located. One of the main appeals of the town is its beachfront, with Savannah Beach being the prominent spot for a suntanning session. Drive a little east to Cape Henlopen for sweeping views of the Atlantic and a bit of World War II history at the Fort Miles Museum.

Come back to downtown to sample some of its best restaurants, from seafood at Striper Bites to the creative French-American take at Heirloom. Being next to the beach, there are great places to stay in Lewes; whether you are after a cozy bed-and-breakfast treatment at Savannah Inn or more of a fancy kind of retreat at Hotel Blue, rest assured you are in the right place for all. 

Bethany Beach

Drone photo of Bethany Beach, Delaware, showing the coastline, beachfront properties, and ocean waves.
Drone photo of Bethany Beach, Delaware.

Bethany Beach is a quieter alternative on the Delawarian coast for a seaside retreat. Attracting mostly families to spend their vacation here, it is the perfect getaway for a mix of solitude and fun for all ages. Lining the golden sand is the Bethany Beach Boardwalk, where several boutiques and gift shops are found for a tax-free shopping spree, and a bandstand that plays live performances for entertainment in the evening. Dine into the culinary delights of this community at Bluecoast Seafood Grill, or enjoy a drink at Mango’s oceanfront deck.

If you are an outdoor enthusiast, just outside of town, there is excellent surfing at Delaware Seashore State Park, while Holts Landing has trails to walk on and a pier for crabbing. There is a wide selection of places to stay here; many vacationers love the large family rooms and location of Bethany Beach Ocean Suites, while further north, Addy Sea Historic Oceanfront Inn provides a more secluded experience. 

Fenwick Island

Colorful beach houses lining the streets of Fenwick Island, Delaware, with vibrant hues and coastal charm.
Colorful beach houses lining the streets of Fenwick Island, Delaware.

The southernmost beachside community of Delaware is right on the state border with Maryland. Fenwick Island draws many visitors not only to its beach but also to the water slides and lazy river rides at Viking Golf Amusements and Thunder Lagoon Water Park, one of the most popular attractions on the coast in the summertime. The same season has the doors of Discoversea Shipwreck Museum open too, with over 10,000 maritime artifacts on display. Towering all the action is the 87ft high Fenwick Island Lighthouse, which offers tours to explore its grounds and museum.

With all that fun, settle down for a meal at Catch 54 for waterfront views, or have a unique dining experience at Just Hooked, a restaurant known for its freshly caught seafood and locally farmed produce. Despite all the excitement of this place, the beachside community still works perfectly as a destination of retreat, as the posh atmosphere of Fenwick Shores has proven to its guests for stay after stay. 

Discover Delaware’s Enchanting Small Towns

From the historic highlights of New Castle to the seashores of Bethany Beach, the state of Delaware is a pocket-sized package for every kind of need in a vacation, especially for a weekend getaway. Coming here for a retreat is an experience you will never forget; whether it is total seclusion or all-inclusive amenities you are after, Delaware can work its way to make your stay a memorable one.

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