Middletown is a fast-developing New Castle County community that’s become a hotspot for young families, new businesses and trendy chains. It’s hard to believe that the quaint community of Odessa—a colonial town that seems to have stood still in time—is just a few minutes down the road from Middletown’s bustling shopping centers.
If you want to spend a day photographing historic scenes, taking in colonial views and learning about Delaware history from knowledgeable guides, spend a day in Odessa. The small-but-mighty Delaware community is also home to some great eats, and the restaurants alone are worth the trip.
For prospective day-trippers to Odessa, there’s plenty to do right in town or a short drive away. Take a look at our guide, then plan your own ideal trip to Odessa.
Don’t forget to tag us (@delawaretodaymagazine) on Instagram if you visit any of these spots!
9 a.m. – Start the day at Corner Grounds Cafe
Corner Grounds Cafe opened in January of 2024, filling a gap in the region for a local coffee shop. The cafe quickly grew a community of regulars thanks to ever-changing flavor specials and unique offerings like coffee flights. Grab a coffee or tea along with a bagel, pastry or yogurt parfait and sit down at a table. With comfortable seating and a cozy atmosphere, it’s a great place to slowly start your morning.
102 North Fifth Street, Odessa
View this post on Instagram
10:30 a.m. – Visit the Corbit-Sharp House
Built in 1774, the Corbit-Sharp House is home to 250 years of rich history. One of the primary draws of this National Historic Landmark is the upstairs room where previous residents hid a runaway slave. Tours of the house highlight the tight space above the stairs where a fugitive slave named Sam hid in 1845 before making his way to Philadelphia. The Corbit-Sharp House is designated as part of the Harriet Tubman Underground Railroad Byway and the National Underground Railroad Network to Freedom of the National Park Service, making it a must-stop on your trip to Odessa.
118 Main Street, Odessa
View this post on Instagram
12 p.m. – Enjoy a classic diner-style lunch at the Odessa Diner
Historic charm radiates throughout Odessa, including its eateries. Enjoy classic American fare in a retro atmosphere at Odessa Diner. Customers love the family-run vibe and diner essentials like sandwiches, chicken soup, pork chops and much more.
3147 Dupont Parkway, Middletown
1 p.m. – Explore Odessa’s other historic landmarks
There’s so much more to explore after the Corbit-Sharp House! The Wilson-Warner house next door was constructed in 1769 to affirm David Wilson’s status as the town’s most prosperous merchant. The historic Pump House was built by William Corbit as housing for his tannery employees and is said to have served as the town jail for a time. The historic gardens behind the Corbit-Sharp House also serve as a stroll through colonial history. It’s easy to spend a few hours sightseeing and photographing these colonial landscapes.
202 Main Street, Odessa
View this post on Instagram
3 p.m. – Take a quick drive to Middletown to Your Creation Station
Less than 10 minutes down the road in Middletown, Your Creation Station is a must-visit for anyone with creative energy to burn. The paint-your-own pottery and walk-in art studio is the perfect place to channel your inner artist. Paint a piece of pottery like a mug, decorative dish, planter and more.
318 East Main Street, Middletown
6 p.m. – Enjoy award-winning food at Cantwell’s Tavern
Odessa is home to a repeat Best of Delaware winner, the historic Cantwell’s Tavern. The dining room reflects the rich history of what was once the Cantwell’s Bridge Hotel and Tavern. The menu includes a raw bar, variety of appetizers, pizza, flatbreads, sandwiches and entrees like short ribs and steaks.
109 Main Street, Odessa
View this post on Instagram
8 p.m. – Turn in for the night at Miller-Dunham House Bed & Breakfast
There’s no better way to end a day filled with historic charm than at a historic B&B. This colonial-style home in the heart of historic Odessa serves as a cozy bed and breakfast with charming gardens, quaint rooms and fresh, homemade breakfast in the morning.
207 High Street, Odessa
Related: What to Do in Lewes: A Day Trip Guide to This Historic Beach Town
