Delaware Town Everyone Should Visit At Least Once
Sitting on the banks of the Appoquinimink River in southern New Castle County, Delaware, Odessa serves as an example of an 18th-century grain shipping port. The town’s origins date back to the 1660s, when Dutch settlers first recognized the value of the Appoquinimink area. Today, much of that historical significance remains visible in the town’s preserved properties and long-standing practices, making Odessa a place many visitors consider worth visiting at least once.
How Odessa Grew to Prominence
The settlement was not originally named Odessa but Apequinemy, adopted from the indigenous name for the region, with the hope of establishing a trade route to the western colonies. In 1664, the English gained control of the territory, and the estate was eventually granted to Captain Edmund Cantwell, the first sheriff of New Castle County in 1672. By 1731, Edmund’s son, Richard Cantwell, received permission to construct a toll bridge over the Appoquinimink Creek. The settlement that grew around this crossing became known as Cantwell’s Bridge.
Apequinemy functioned as a vital link between local farms and the maritime trade routes of the Delaware River. Goods moved along the Old Hermann’s Cartroad, a historic path connecting the Appoquinimink Landing to Bohemia Manor in Maryland. This geographic advantage allowed Cantwell’s Bridge to flourish as a grain-shipping center. However, the arrival of the railroad in nearby areas during the 1850s threatened the town’s river-based economy. In an effort to rebrand the community as an export hub, town officials renamed it Odessa in 1855 after the Black Sea grain port.
The Architectural Core and the Historic Odessa Foundation
The preservation of the town today is largely the result of the 1930s efforts of H. Rodney Sharp, a preservationist and former schoolteacher who married into the DuPont family. Sharp spent decades purchasing and restoring local properties, often moving historic structures to prevent their demolition. His work laid the groundwork for the Historic Odessa Foundation (HOF), which now manages a collection of museum houses that provide a close view of early American life.
The Corbit-Sharp House, completed in 1774, is the most prominent structure in the collection. William Corbit, a Quaker tanner, commissioned architect Robert May to build the five-bay, twenty-two-room mansion. It is considered one of the finest examples of Philadelphia-style Georgian architecture in the region.
Next door, the Wilson-Warner House provides a contrasting narrative. Built in 1769 by David Wilson, a successful merchant, the house reflects the Delaware-Georgian style. Wilson’s professional success was eventually undermined by financial misfortune, culminating in a bankruptcy auction in 1829. This legal crisis preserved a detailed historical record of the home; the "List of Sale" from the auction provided a line-by-line account of the family’s possessions, from kitchenware to fine furniture. The house was eventually bought back and restored by Wilson’s great-granddaughter, Mary Warner, in 1901.
Economic Anchors and Adaptive Reuse
These days, Odessa’s economy depends on a small number of long-standing businesses operating out of historic buildings. Just look at Cantwell’s Tavern. Back in 1822, it was built as the Cantwell’s Bridge Hotel and Tavern, where travelers and locals could meet, talk politics, or just hang out. Now, after some serious restoration work, it’s back up and running as a restaurant, using local ingredients like those that make up its daily raw bar, and has become a place for hearty dishes like the Southern Fried Chicken Sandwich entrée or Short Rib Stroganoff.
For those looking for fresh, homemade Italian fare with a loyal following in Odessa since 1991, check out Lorenzo’s right on Main Street. It is a family-run spot operating out of a converted household, and you can get something for the whole squad here, ranging from pizzas and wings to cheesesteaks and a range of homemade desserts.
Annual Events and Community Engagement
Life in Odessa is shaped by tradition. Every year, when Christmas arrives, the town hosts a celebration known as Christmas in Odessa. People attend from both within the community and beyond for a holiday event that has continued for more than half a century. One of the main attractions is the opportunity to step inside private homes from the 1700s and 1800s, buildings typically viewed only from the street. In addition to home tours, tickets include access to other events throughout the day, including meeting Santa, a Gingerbread House Contest, refreshments, and performances by local choirs.
Towns to Visit Near Odessa
Odessa makes a perfect jumping-off point for checking out nearby towns. Head south and you’ll hit Smyrna, where the 1870 Smyrna Opera House stands out with its Second-Empire style. They still put on shows and art exhibits, so there’s almost always something happening. Don’t skip the Smyrna History Museum either. They’ve got the Plank House, which is one of the last Swedish Delaware plank-dwelling examples from the late 1700s still standing.
Drive west, and you’ll land in Middletown. Here, the Everett Theatre still puts on performances. You might recognize this location from the movie Dead Poets Society. Middletown is loaded with places to eat and shop, too, making it a good place to explore and enjoy during your Odessa holiday.
If you go east, Delaware City offers a whole different vibe. It’s got a riverfront and a ferry to Fort Delaware State Park on Pea Patch Island. Step off the boat, and you’re in a Civil War-era fortress, with costumed guides who bring the history of soldiers and prisoners to life.
Why Odessa’s Preservation Still Matters
Odessa has been a settlement that has survived and adapted in the Delaware territory since the mid-1600s. This history is visible throughout the town, from historic homes opened for seasonal walking tours to the restored Cantwell Tavern. With connections to nearby towns and communities, Odessa also serves as a practical starting point for exploring the surrounding region. For those interested in American history, the town offers a concentrated view of the forces that shaped this part of the state.
