Plan A Trip To Odessa, One Of Delaware’s Best Small Towns

Since Delaware is the “First State”, it’s clear that you’ll find a whole lot of history here! Some of our most charming towns are also our oldest, and a visit to the historic Delaware town of Odessa will show off Delaware’s history and charm. Enjoy a peaceful walk through the well-manicured gardens and landscapes, learn about early Delawareans, and enjoy a meal in a 200-year-old building! After just one visit, you’ll understand why Odessa is one of the best small towns in Delaware.

During these uncertain times, please keep safety in mind and consider adding destinations to your bucket list to visit at a later date.

Check out an interactive map of all that the historic Delaware town has to offer thanks to the Historic Odessa website, here. See if there are any events on the calendar before you plan your trip! You’ll never want to leave one of the best small towns in Delaware – Odessa!

If you’re interested in learning more about the history of Cantwell’s Tavern, Odessa, and the earliest days of the town’s history as a train stop, read The Timeless Delaware Restaurant Everyone Needs To Visit At Least Once.

Address: Odessa, DE, USA
The OIYS Visitor Center

Best Small Towns In Delaware

July 29, 2021

What are the most charming small towns in Delaware?
Almost all of Delaware’s towns are small, and lots of them are packed with charm. If you love beautiful rolling hills and lots of places to shop and dine, visit Hockessin. Down on the bay, Bowers Beach is a contender for the most charming small town in Delaware. Be sure to visit the Bowers Maritime Museum to learn all about shipwrecks and pirates! If you continue farther south, you’ll find yourself running into Fenwick, which is a unique town right on the border of Delaware and Maryland that’s a picturesque seaside town.

Which historic towns in Delaware have remnants of the past?
If you love history, visit the First State! Delaware is home to a National Historical Park that celebrates the footprints of the past you’ll find here. Visit New Castle, Odessa, Yorklyn, Lewes, Georgetown, and Dover if you truly want to see the past. Each of these towns and cities offers museums, historical architecture, and so much more. You’ll feel like you’ve stepped back in time, and you’re sure to learn all about the First State as you travel through.

Are there any scenic road trips in Delaware?
Delaware is home to several scenic byways worth driving. Of course, the most famous scenic road trip takes you down the Delaware Bay into the town of Lewes, on Cape Henlopen. This is where the bay meets the ocean, and you’ll enjoy the coastal views all the way down. Other scenic byways include the Nanticoke Heritage Byway in western Sussex County and the Red Clay Valley Scenic Byway that winds through the Brandywine Valley.

Address: Odessa, DE, USA