Talbot County’s Holiday Season Guide

‘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:

Sea Glass Festival in Talbot County, Maryland.

Eastern Shore Sea Glass and Coastal Arts Festival Holiday Edition

November 19-20, 2022 | 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.

Festival of Trees

November 25-29, 2022 | 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 on November 26, 2022 and Santa’s 5K Run on November 19, 2022.

Shop Small Saturday in Easton

November 26, 2022 | Easton

On the last Saturday in November, support small businesses during the #ShopSmall event in downtown Easton. Shop owners will roll out the red carpet on one of their busiest shopping days of the year. Downtown Easton storefronts include women’s and men’s clothing boutiques, antiques, art galleries featuring local artists and craftspeople, and so much more. You’ll have no problem checking items off your list.

Easton’s Moonlight Madness

December 2, 2022 | Easton

Celebrate the Holidays at the Moonlight Madness Shopping Event in Downtown Easton! Downtown shops and restaurants will be open until 10 p.m. serving refreshments and snacks, and featuring holiday gifts to buy. Enjoy music and entertainment throughout the town as you ring in the holiday season!

Christmas on the Creek

December 2-4, 2022 | Oxford

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. Start with a Bluegrass Nutcracker at the Oxford Community Center on Friday, December 2nd, with the weekend bringing a Christmas Bazaar, Holiday Tea at the Robert Morris Inn, Caroling at Pope’s Tavern, Santa in Town Park, shops open for gift buying, and so much more!

Easton’s Holiday Parade

December 3, 2022 | 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 6 p.m. with parade getting underway at 6:30 p.m.

Midnight Madness in St. Michaels

December 3, 2022 | St. Michaels

As day turns to night, St. Michaels becomes a beautiful twinkling Christmas Village.  Shops will be open late with refreshments and snacks, and 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 start at 11:00pm at The Galley Restaurant and participants must be present to win. Event starts at 4 p.m.

Christmas in St. Michaels

December 9-11, 2022 | 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 ParadeSanta DashTour of HomesLighted Boat Parade, performances of holiday music, and so much more. Plus, St. Michaels mile-long shopping district!

An Island Christmas

December 17-18, 2022 | Tilghman Island

Celebrate Christmas watermen-style on Tilghman Island. The village will herald in the holiday season with a lighted boat parade, caroling, and the lighting of the crab basket Christmas tree!

First Night Talbot

December 31, 2022 | Easton

First Night Talbot 2022 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 2023!

Easton Carriage Rides


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 eventswhere 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!

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