History, Holidays, and Hospitality in Historic Odessa

Nestled along the Appoquinimink River, Historic Odessa, Delaware is one of those small towns that feels like stepping back in time. Once known as Cantwell’s Bridge, this 18th-century port town was renamed Odessa in 1855 — a nod to the Ukrainian seaport and its own hopes for growth. Today, it’s a beautifully preserved slice of Delaware’s history, filled with charm, brick-lined streets, and timeless architecture.

A Spontaneous Visit Turned Special

With a little unexpected free time, I finally made the trip to Odessa — a place that’s been on my must-see list for years. The friendly receptionist at the Visitor Center welcomed me (and another couple who’d just stopped in) and quickly added us to an ongoing tour. We caught the second half of one tour and the first half of another — both led by fantastic guides who made us feel right at home.

Our second guide, Elaine, a retired history teacher and Underground Railroad specialist, was especially engaging. Her stories made the houses and their past residents come alive. I’m already plotting my return to catch one of her specialized tours!

What You’ll See

Odessa’s guided tours include the Corbit-Sharp House, Wilson-Warner House, and Collins-Sharp House — all furnished with authentic 18th- and 19th-century pieces. You’ll see polished wood floors, working hearth kitchens, elegant dining tables set for guests, and children’s rooms with handmade toys. Each space reveals how early Delaware families lived, worked, and even fought for freedom.

From November 11 through December 31, 2025, two special exhibits add extra charm:

• Jane Austen’s 250th Celebration – Themed exhibits and programs honor the beloved author’s legacy.

• Storybook Trees Exhibit – Christmas trees decorated to represent classic children’s stories — a local favorite for all ages.

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Christmas in Odessa – December 6th

The highlight of the season is Christmas in Odessa on December 6th, when the entire town transforms into a festive wonderland. Historic homes open their doors, dressed in greenery and candlelight, while live music, artisan vendors, and colonial reenactments fill the streets.

Ticket sales support the Historic Odessa Foundation’s preservation efforts as well as fund college scholarships for local high school seniors in the Appoquinimink School District.

Don’t Miss Cantwell’s Tavern

You know I love a good place to eat! After your tour, stop by Cantwell’s Tavern, a beautifully restored 1800s gathering place right in the heart of town. With hearty, locally inspired dishes and friendly service, it’s the perfect spot to relax after a day of exploring — I’ve eaten there myself, and it was such a fun experience.

Whether you love history, the holidays, or simply charming small towns, Historic Odessa deserves a spot on your list. Come for the story, stay for the spirit, and don’t miss the magic this December!

Find out more info on hours, pricing, and events here on their website.