Delaware's Charming Colonial Town Is A Historic Haven With A Quaint Downtown And Preserved Architecture

Although often overlooked, the small state of Delaware really packs a punch with its historical significance. The first state to ratify the United States Constitution is home to a number of quaint towns that are well worth a visit if what you're looking for is a glimpse back in time, and Odessa is top on our list. As one of the oldest towns in Delaware, Odessa dates all the way back to the 1660s when the area first became a Dutch settlement. The Federalist architecture and gorgeously restored homes that draw visitors today are a result of the hamlet's riverside location, which made it an important grain shipping port after the English took control of the area in 1664.

By the 1730's the town formerly known as Cantwell's Bridge was bustling. Its important commercial role along the Delaware River persisted for well over a century, but the railroad introduced in 1855 served as a more cost-effective option for transporting goods. The competition delivered a blow to the local economy that Cantwell's Bridge would never recover from, and not even the new name of Odessa – chosen to bring to mind the success of another well-known wheat port in southwestern Ukraine – could save the town's commercial status. 

Today, Odessa boasts an unmatched charm that will capture the heart of any tourist with an eye for colonial architecture and an ear for history, and its proximity to other Delaware destinations like Wilmington and New Castle, another riverfront city frozen in time with cobbled streets and European charm, make it an easy addition to any road trip in the area. Read on to learn about the local businesses and historic sites that make this unknown treasure a desirable place to visit all on its own.

Odessa is just a short 24 mile trek from the affordable weekend getaway of Wilmington where you can catch a flight at the Wilmington Airport (also known as New Castle Airport). It's also only 43 miles down I-95 from the Philadelphia International Airport, making it possible to land from an international destination and reach the quaint tree-lined streets of Odessa in under an hour. Philadelphia is called America's Garden Capital for a reason, so if browsing beautiful blooms is on your agenda, you're in luck — there are over 30 noteworthy gardens to choose from within a 30 mile radius, making this journey from a bustling city to a slower-paced township a satisfying ride full of possibilities.

Once you reach Odessa, which boasted a whopping population of just 362 people in 2024, you'll find out how close-knit this special community really is. Grab your morning caffeine fix at Corner Grounds Cafe, where the responsibly-sourced coffee and cozy lounge keep the locals coming back day after day, or if classic diners are more your speed you can visit the Odessa Diner in neighboring Middletown.

As the town was formerly known as Cantwell's Bridge, the repeat Best of Delaware winner Cantwell's Tavern is a restaurant that can't be missed, serving up a side of history along with their award-winning food. Built in 1822 by William Polk, the Cantwell's Bridge Hotel and Tavern operated for over 100 years as one of five different taverns frequented by visitors to the important shipping port, and the decor of the restaurant's dining room today aims to stay true to those roots.  The menu boasts a raw bar, sandwiches and flatbreads, and a selection of entrees including salmon and steak.

When it comes to pristinely preserved historic sites and homes, look no further than the Historic Odessa Foundation. Incorporated in January of 2005 with the goal of preserving and sharing Odessa's history with the public, the Foundation's impressive museum collection houses more than 7,000 regional objects dating from 1760 to 1850, and the grounds and gardens span nearly 30 acres through the heart of town. Guided walks are offered through their five main properties from March to December, and the number one site to see happens to be one of Delaware's 13 National Historic Landmarks. The Corbit-Sharp House, which also has ties to the Underground Railroad as a National Parks Service Network to Freedom site, is one of two such sites found in Odessa, the other being the Appoquinimink Friends Meeting House and Cemetery.

Other must-see locations include the Wilson-Warner House, which dates back to 1769 as the former residential home of one of Odessa's most successful merchants; the Collins-Sharp House, which was built in 1700 and stands as one of Delaware's oldest structures; and the Pump House, which may have served as the town jail during the 18th century. Cantwell's Tavern, which opened in 1822 as a hotel and tavern and began running as a restaurant again in 2012 is well worth a visit, and the old Odessa Bank, which operated as the First National Bank of Odessa, now serves as the town Visitor's Center. 

The opportunity to support the local preservation efforts of the Historic Odessa Foundation is reason enough to visit one of Delaware's hidden gems. Whether you're looking for a glimpse back over the centuries or just a quiet weekend away, the local charm and beautiful colonial architecture of Odessa promises a special experience you won't soon forget.