‘Tis the season to be transported to another world, where life ambles at a more leisurely pace, the hospitality is warm and welcoming, and the cozy, luxurious accommodations and eateries fill you with the festive spirit.
The communities of Talbot County transform into a festive wonderland during the winter holiday season. With twinkling lights illuminating town streets, candlelit dinners by warm fireplaces, horse-drawn carriage rides, and shops decorated for Christmas, you’re sure to be jolly and ready to join in the many holiday events and activities.
Here’s Our Guide on How to Get Festive in Talbot County:
Eastern Shore Sea Glass and Coastal Arts Festival Holiday Edition
November 23, 2024 | St. Michaels
The Eastern Shore Sea Glass and Coastal Arts Festival returns for the holiday season and brings artisans and craftspeople exhibiting and selling coastal and sea-glass related jewelry, home décor, art, and more. Plus, live music, and entry to all of the exhibitions and historic structures on the campus of the Chesapeake Bay Maritime Museum. Food and beverages will be available for purchase, including beer, wine, and cocktails. Tickets will also be available at the door. You’re sure to find something unique for someone on your holiday list.
November 30 – December 3, 2024 | Easton
Over Thanksgiving Weekend, Christmas trees are beautifully decorated according to the theme of the season and displayed at historic downtown Easton’s Tidewater Inn. Some trees are even available for purchase. Highlights of this event also include Carols by Candlelight and Santa’s 5K Run.
November 30, 2024 | Easton
On the last Saturday in November, support small businesses during the #ShopSmall event in downtown Easton. Downtown Easton storefronts include women’s and men’s clothing boutiques, antiques, art galleries featuring local artists and craftspeople, and so much more. While you’re out, stop by the Talbottown Shopping Center to Talk to Rudolph. This long-standing Talbot County tradition runs through December 22. You can continue to check items off your list during Starlight Shopping in downtown Easton on December 7, 14, and 21 where shops stay open late and free carriage rides add a festive spirit.
November 29 – December 18, 2024
The waterfront Town of Oxford transforms into a holiday wonderland, beginning with Shop Small-Shop Local on November 29 with events running through December 18. See the beautiful historic homes lit for the holiday and the lighted crab pot trees twinkling at the end of every dock as the town of Oxford celebrates Christmas on the Creek. The events brings a Lighting of Dock Trees, Posadas in Oxford, Christmas Market, Cookie Walk, Breakfast with Santa, a Holiday Market, caroling, and so much more!
December 7, 2024 | Easton
On the first Saturday of December, Easton starts with a downtown Christmas tree lighting then cheers on the parade of floats, classic cars, local bands, and Santa himself as they traverse the one-mile route. Make a day of it by coming downtown early for some holiday shopping, grab a bite to eat, and then find a great spot along the route to watch the parade. Tree lighting takes place at 5:30 p.m. with parade getting underway at 6:30 p.m.
Midnight Madness in St. Michaels
December 7, 2024 | St. Michaels
As day turns to night, St. Michaels becomes a beautiful twinkling Christmas Village. Shops will be open late with refreshments and snacks, offering special sales during Midnight Madness. Plus each purchase at participating businesses gives you a chance to win raffle prizes valued at over $15,000. Drawings are held at The Galley Restaurant and participants must be present to win.
December 13-15, 2024 | St. Michaels
Visit St. Michaels during the second weekend in December when the streets are decorated with cheerful lights, the Hooper Straight Lighthouse at the Chesapeake Bay Maritime Museum is dressed up for the season, and The Christmas Shop is ready to help you stock up on your own charming holiday décor. The weekend is filled with events including Breakfast with Santa, the Talbot Street Parade, Tour of Homes, Lighted Boat Parade, performances of holiday music, and so much more. Plus, St. Michaels mile-long shopping district!
December 31, 2024 | Easton
First Night Talbot will celebrate the New Year in crabby style! Performances will take place throughout the evening, culminating in the Crab Drop at midnight. Enjoy a New Year’s Eve dinner at one of Talbot County’s many restaurants then head to the corner of Dover and Harrison Streets to welcome 2025!
Easton
Step back in time with a carriage ride through the streets of Easton to see the beautiful homes and shops illuminated for the holidays. Reserve a weeknight tour for up to six people, then dress up warm, bring a blanket, and brush up on your Christmas carols as you and your family or friends experience the season in a whole new light. Thirty minute rides run from Thanksgiving through Christmas. Reserve now as rides sell out fast!
See our other holiday events, where to sip some holiday cheer or a chef-inspired meal, and a place to stay while you get into the festival spirit here in Talbot County!
