Take This Road Trip Through Delaware’s Most Picturesque Small Towns For A Charming Experience
Tiny Delaware is filled with tiny towns, and sometimes you just need to get off of the main roads and explore your state to see things you never knew were there. There’s no reason to only stay on Route 1 or Route 13 every time you travel downstate! I’ve put together a map of nine picturesque, charming, quaint and historic small towns in Delaware for you to explore – and the routes between them are mainly back roads, where you’ll see the First State like you never have before.
Click here for an interactive, town-by-town map of the trip.
Claymont is a New Castle County town that's been reviving historic sites for the past 20 years, and it's becoming more charming, historic and beautiful than before. Explore downtown and learn about new sites that are being preserved every year.
I love Hockessin - it's so beautiful, all year long. In the spring, Mount Cuba hosts an incredible wildflower celebration, in the summer there are amazing street festivals and fairs, in the fall it is stunningly beautiful, and in the winter, the town goes all out with Christmas spirit.
The historic homes of Odessa on Main Street are the best Christmas attraction in Delaware every year, when they open for holiday home tours. This is one stop you will absolutely love.
Wyoming is a quiet, quaint town and the back roads around the town will show you rural Delaware in a completely new light. Stop by Fifer Orchards to see a beautiful farm and pick up some fresh produce or an apple cider donut.
Visiting Felton, you'll feel like you've traveled back in time. This quaint town of under 1,000 people boasts a vintage train station and gorgeous Victorian houses.
Downtown Milford is one of the best little downtowns in Delaware, and the vendors and merchants always have something going on. Visit during the holidays for a festive time and to see beautiful decorations.
Seaford was voted 28th Best Small Town in America at one point and is full of parks, historic sites, museums and mouthwatering restaurants. Be sure to spend some time exploring this town.
Millsboro is one of the tiniest towns on our list, but it is filled with historic sites that are worth seeing! Be sure to see the Robert Davis and Isaac Harmon Farmhouses, the Perry-Shockley House, Warren's Mill, The Indian River Archeological Complex, and the Ames Hitchens Chicken Farm.
Selbyville is my pick for a tiny beach town to end your Delaware Small Towns Road Trip because of the unbelievable restaurants this little spot has to offer. The Lobster Shanty is an absolute favorite, as is Captain Mac's Fish House. So after a long time on the road, drive through the adorable, quaint town and stop at any of the restaurants you see - they're all delicious.
If you love our Delaware Road Trips, you should check out our winter wonderland trip to see the most incredible Christmas Lights in Delaware.
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