Holidays on the Eastern Shore

The holiday season is a special time on Maryland’s Eastern Shore, where the historic charm of waterfront towns like Easton, St. Michaels, Oxford, and Cambridge comes alive with festive events, parades, and plenty of cheer. Whether you’re visiting for a weekend or planning to settle into the Eastern Shore’s unique lifestyle, these holiday events offer something for everyone. Here’s your guide to making the most of the season in these picturesque communities.

Easton, MD: A Hub of Holiday Festivities

1. Christmas in Easton - Festival of Trees Kick off the holiday season with a visit to Easton’s renowned Festival of Trees, a spectacular event featuring beautifully decorated trees in all shapes and sizes. Hosted by the Talbot Hospice Foundation, this event showcases the talents of local designers and raises funds for a great cause. Take a leisurely stroll among the twinkling lights and artistic displays, and let the festive spirit inspire your holiday decor!

When: Thanksgiving weekend
Where: Tidewater Inn

2. Holiday Parade & Tree Lighting Easton’s Holiday Parade and Tree Lighting ceremony is a beloved tradition that delights locals and visitors alike. Enjoy a festive parade, live entertainment, and the lighting of the town’s Christmas tree in Thompson Park. Santa himself will make a guest appearance to greet children and spread some holiday cheer!

When: First Saturday in December
Where: Downtown Easton

3. Easton’s Midnight Madness Shopping Event Get a head start on your holiday shopping with Easton’s Midnight Madness! Shop local businesses, enjoy special holiday discounts, and maybe even meet Santa as you browse unique gifts along Easton’s historic streets.

When: December, date TBA
Where: Downtown Easton

St. Michaels, MD: A Classic Christmas by the Bay

1. Christmas in St. Michaels One of the most anticipated holiday events on the Eastern Shore, Christmas in St. Michaels is a multi-day celebration featuring a holiday parade, a display of decorated homes, and a Holiday Marketplace with local vendors. The event supports local nonprofits and brings the community together for a season of giving. Don’t miss the Talbot Street Parade, a highlight with festive floats and marching bands.

When: Second weekend in December
Where: Downtown St. Michaels

2. The Annual Boat Parade For a holiday event unique to waterfront towns, catch St. Michaels’ Annual Lighted Boat Parade. Local boaters deck their vessels with lights and decorations, creating a dazzling parade along the Miles River. It’s a magical experience for all ages and a fantastic photo opportunity!

When: December, during Christmas in St. Michaels weekend
Where: St. Michaels Harbor

Oxford, MD: A Cozy Coastal Christmas

1. Oxford Christmas on the Creek Experience Oxford’s Christmas on the Creek, a quaint celebration with carolers, a tree lighting ceremony, and Santa arriving by boat! The festivities often include holiday crafting, hot chocolate stations, and a chance to take in Oxford’s charm as it’s decorated for the season.

When: December, typically the weekend before Christmas
Where: Oxford Park and surrounding areas

2. Oxford Holiday House Tour The Oxford Holiday House Tour is a treat for architecture enthusiasts and holiday lovers alike. Explore historic homes dressed up for the season with lights and decorations. The tour provides a rare chance to see inside some of Oxford’s finest homes while supporting local nonprofits.

When: Mid-December
Where: Various historic homes in Oxford

Cambridge, MD: A Vibrant Holiday Spirit

1. Cambridge Main Street’s Holiday Parade Cambridge’s Holiday Parade is the biggest of the year, featuring floats, live music, and Santa. This parade brings the entire community together and lights up downtown Cambridge with excitement. Stick around afterward to enjoy hot cocoa and local shops open for holiday shopping.

When: First Saturday in December
Where: Downtown Cambridge

2. Christmas Train Garden at the Cambridge Rescue Fire Company The Christmas Train Garden is a beloved Eastern Shore holiday tradition. Families can enjoy intricate model train displays, complete with seasonal scenes, miniature villages, and snowy landscapes. Each year, the displays grow more creative, with interactive elements that delight both kids and adults.

When: December 1-31
Where: Cambridge Rescue Fire Company

3. Santa Swim at the Hyatt Regency Chesapeake Bay The annual Santa Swim raises funds for local charities and is a must-see event! Brave souls dive into the cold waters of the Choptank River, often in festive attire, to support a great cause. The event is fun for spectators and participants alike, with prizes for the best costumes.

When: Mid-December
Where: Hyatt Regency Chesapeake Bay Resort

Celebrate the Season with a Stay on the Eastern Shore

With so many holiday events across Easton, St. Michaels, Oxford, and Cambridge, there’s no better time to experience Maryland’s Eastern Shore. Whether you’re exploring the historic streets, joining in a holiday parade, or simply enjoying the lights and decorations, these towns offer an unforgettable holiday experience. So gather your friends and family, bundle up, and come enjoy the magic of the season on the Eastern Shore.

Happy Holidays from Maryland’s Eastern Shore!