Delaware is a state full of small towns, and that means we’ve got some great Main Streets. If you’re looking to enjoy the small town feel, you’ll love walking from shop to shop and checking out local cafes and restaurants in these 8 best walkable towns in Delaware.

1. Main Street, Middletown
Main Street, Main St, Middletown, DE, USA
Flickr / Ismo
Middletown is one of the most charming towns in the state! With plenty of restaurants, historic buildings, shops, and the Everett Theater, you'll never run out of things to do when you visit. It's especially fun to visit in October, as it's the best Halloween town in Delaware.
2. Market Street, Wilmington
North Market Street, N Market St, Wilmington, DE, USA
Facebook / New Market Wilm
Market Street in Wilmington has undergone some serious rejuvenation in the past few years, and if you haven't been here recently, you might not recognize it! There are so many new cafes, bars, restaurants and shops to explore that you'll never want to leave.
3. Loockerman Street, Dover
West Loockerman Street, W Loockerman St, Dover, DE 19904, USA
Flickr / Mike Mahaffie
Loockerman Street is Dover's Main Street, and it does an amazing job of capturing the allure of this historic Delaware town. Pick up food from one of the many restaurants and have a picnic on the green, or stay warm and cozy inside any of the award-winning restaurants surrounding it.
4. Main Street, Newark
Main Street, Main St, Delaware, USA
Flickr / Yuh-Jen Shih
Main Street in Newark has everything you could possibly want - breakfast cafes, hippie clothing shops, a 5 and Dime, a mouthwatering gelato shop, bars, and elegant restaurants. You could easily spend a day browsing everything in the heart of town. Visit Newark at Christmastime for a truly magical experience.

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5. Rehoboth Avenue, Rehoboth Beach
Rehoboth Avenue, Rehoboth Ave, Rehoboth Beach, DE 19971, USA
Facebook / Rehoboth-Dewey Chamber of Commerce
While some might consider the Boardwalk to be Rehoboth's Main Street, I think Rehoboth Ave makes a strong case. During festival weekends, it's packed with vendors and during quiet weekends, the shops are still filled with visitors. You can find all sorts of great food and shopping here, and you'll only ever be a few steps away from the beach. Learn more about Rehoboth Beach, the friendliest town in Delaware.
6. Market Street & The Circle, Georgetown
East Market Street & The Circle, E Market St & The Cir, Georgetown, DE 19947, USA
Flickr / Eric B. Walker
Georgetown is a quiet little town, but Market Street and the Circle are always bustling with life. Whether you track down a food truck or dine in a brick-and-mortar restaurant, you'll enjoy whatever you eat here, and the history you'll stroll by is mesmerizing.
7. Riverwalk, Milford
Mispillion Riverwalk, 103 S Washington St, Milford, DE 19963, USA
Facebook / Downtown Milford, Inc.
The Riverwalk in Downtown Milford is always busy with visitors and natives alike! Whether it's for a festival, concert, farmers market, food truck event, or just on a nice weekend afternoon, you'll love the view of the river and the people that you meet along the way.
8. Delaware Street, New Castle
Delaware Street, Delaware St, New Castle, DE 19720, USA
Flickr / Ken Lund
Historic New Castle's Delaware Street shows off the best of Colonial Delaware. From tasty meals at Jessop's Tavern to historic old homes, you'll feel like you've stepped back in time as soon as you step out of the car.

 

If you love trying new restaurants, keep an eye out for 8 of the Best Main Street Restaurants in Delaware Hiding in Plain Sight when you’re walking downtown in any of these peaceful places.

Are there any towns you love that didn’t make our list of the best main streets in Delaware? We’d love to hear about them.

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More to Explore

Best Walkable Towns In Delaware

Meghan Byers | June 16, 2022

What are some other unique towns to visit in Delaware?

There are so many charming towns in Delaware. The little river town of Millsboro makes for a wonderful and unique Sussex County day trip, with a picturesque downtown including a historic restaurant. For more history in Sussex County, visit beautiful Laurel, Delaware, which has a long list of buildings on the National Register of Historic Places. And for beachfront charm, don’t forget the First Town in the First State – lovely Lewes, located at the tip of Cape Henlopen.

What are the smallest towns in Delaware?

From the artist’s haven of Arden to the historic former shipbuilding hub of Bethel, Delaware has its share of tiny towns. Henlopen Acres, Odessa, Magnolia, and Leipsic are just a few of Delaware’s smallest towns, and they each have their own unique charm making them worth a visit. The absolute smallest town in the entire state is the village of Hartly in Kent County, with a total area of only 0.1 miles and a population of 73, according to the 2020 census.

What are the best beach towns in Delaware?

Rehoboth Beach, Bethany Beach, and Dewey Beach are all popular for good reason! But there are more beach towns equally worth visiting in Delaware where you may be able to beat the crowds. For example, Fenwick Island is between Bethany Beach and Ocean City, Maryland, but tends to be much quieter - while still being family friendly. Beautiful Fenwick Island State Park has three miles of ocean beaches to enjoy, and the town of Fenwick Island has some classic shoretown shopfronts to explore. You’ll also, of course, find lots of delicious seafood, and there’s a waterpark in town that’s perfect for the kids. Visit our guide to more little-known beaches in Delaware.

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