There are so many pretty small towns in Delaware that make up for their small populations with huge amounts of charm. The best small towns in Delaware are all surrounded by natural beauty, inhabited by the kindest people you’ll ever meet, and home to some of the best restaurants in the First State. Plan a day trip to visit them!

1. Hockessin
Hockessin, DE, USA
Flickr / James Walsh
Hockessin is a little getaway in northern Delaware, not far from busy Wilmington. Explore the town and you'll find charming shops and restaurants, old train tracks, historic covered bridges, and the stunning scenery of the Red Clay Creek.
2. Middletown
Middletown, DE, USA
Flickr / Doug Kerr
Middletown might not be "little" by Delaware's standards, but it's still got that small town feel on Main Street. Enjoy a meal at Sully's Irish Pub and check out the shops and galleries all around you.
3. Georgetown
Georgetown, DE 19947, USA
Flickr / Eric B. Walker
I could spend all day exploring the circle area of Georgetown. This historic Delaware small town is so beautiful - and full of amazing restaurants.
4. Rehoboth Beach
Rehoboth Beach, DE, USA
Flickr / Jason Pier in DC
Rehoboth Beach is Delaware's resort town and it's full of life all year round. In fact, many people like to visit best in the off-season, when the tourists go home but the locals keep the shops and restaurants open.

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5. Dewey Beach
Dewey Beach, DE 19971, USA
Flickr/ Meg Diver G.
Visiting Dewey in Summer and Winter is like visiting two completely different towns. This pretty town quiets down a lot when Labor Day comes, and it's one of the most peaceful coastal towns in the state from September to May.
6. Fenwick Island
Fenwick Island, DE, USA
Flickr / Lee Cannon
Fenwick is a small town just north of Ocean City, MD, so it's got a fun mix of touristy Sunsations stores and charming small town boutiques. The restaurants here that stay open year round are worth the drive down from New Castle County.
7. Bethany Beach
Bethany Beach, DE, USA
Flickr / Webbshots
Compared to the other Beach towns, Bethany is the quietest year round. The nature center is the perfect place to bring your family for an educational and fun day trip and it's one of the pretty small towns in Delaware that everyone loves.
8. Milford
Milford, DE 19963, USA
Downtown Milford
Milford is the most charming river town in Delaware, and no matter when you visit, you'll fall in love. Check it out soon to enjoy the last of the fall foliage before winter begins.
9. Laurel
Laurel, DE 19956, USA
Facebook / Trap Pond State Park
Laurel is one of the most underrated small towns in Delaware. It's full of history and absolutely surrounded by natural beauty! Visit Trap Pond State Park and dine at Abbott's on the Waterfront for a scenic stay in this pretty small town in Delaware.

What do you think are the best small towns in Delaware? Do you like to visit them when the weather gets chilly or would you prefer to wait until spring? If no matter what time you travel, you are always in search of the best eats, then you should take a look at our list of favorite Delaware hole-in-the-wall restaurants.

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More to Explore

Exploring Delaware

Sara Dager | September 19, 2022

What are the most fun and free things to do in Delaware? 

There are a plethora of fun and free things to do in Delaware for the whole family. On the more obvious end is visiting one of our many stunning beaches or parks, and you absolutely do want to take advantage of those, but there is so much more! You can visit an antique Victrola museum or discover gorgeous modern art at the Delaware contemporary. For the animal enthusiasts, in the winter months, admission to the zoo is free. It's a blast to see how the animals' behaviors change when it becomes chilly. Delaware is also home to the Dogfish Head brewery and their free tours were named one of the ten best tours in America!

Which hikes are the most scenic in Delaware? 

If you want to see the most beautiful nature in the first state without too much strenuous hiking, then the easy Delaware hike through the Azalea Woods in Winterthur is a perfect choice. To be fair, this may be more of a stroll, but the stunning gardens are one of the most impressive feats of landscaping in America and the paved ground makes this journey accessible for all levels of ability. If you want to feel like you've earned your visual reward, then you can step out onto the North Delaware Greenway. This hike clocks in at 10.4 miles and is well worth it. You will pass through more than one state park and see large rock formations, gorgeous forests, and even waterfalls.

What are the coolest attractions in Delaware? 

It's hard to nail down the absolute best thing to do in the First State, but there are a few that top the list of the coolest attractions in Delaware. You can ride an actual pirate ship in Wilmington! The Kalmar Nyckel is a perfect recreation of a 17th-century ship that runs popular Pirate themes cruises the whole family will love. Or maybe you're looking for something more relaxing. Then, we recommend a stroll through the breathtaking lavender fields at Warrington Manor. No matter your speed, Delaware has something fun for you.

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