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


See the Christmas Lights of Easton with 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 your weeknight tour for up to six people, then dress up warm, bring a blanket, and brush up on your Christmas carol songbook as you and your guests experience the season in a whole new light.

Thirty minute rides run from Thanksgiving through Christmas. Reserve now as rides sell out fast!

Festival of Trees Brings a Full Weekend of Celebrations

Events take place November 27-30, 2021. Check website for event days and times.

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! The festival also includes a Saturday morning 5K run and evening carol sing.

  • Carols by CandlelightChoral groups, bell ringers, and musicians lead the assembled in traditional Christmas songs, creating a magical, candlelit ambiance in front of the Tidewater Inn.
  • Santa’s 5K Run: Walk or run along the Easton Rails to Trails, passing the Frederick Douglass mural and old train station for a physical challenge, to meet new friends, and all for a good cause. (Takes place December 11)

Get a Jump on Your Gift List During Shop Small Saturday in Easton

We always appreciate it when you shop local, but this special event takes place on November 27, 2021.

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.

Holiday Shopping is Made Fun During Easton’s Moonlight Madness

Get items checked off your list on December 2, 2021 from 4 p.m. to 10 p.m.

On the second Thursday of December, Easton’s shops open at 4 p.m. and stay open to 10 p.m. for a fun and festive holiday shopping experience. There are chances to win raffle prizes and listen to live music. Stores may even offer hot beverages to help keep you warm.

Easton’s Holiday Parade Gets the Season Rolling

On December 4, 2021, tree lighting takes place at 6 p.m. with parade getting underway at 6:30 p.m.

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.

Ring in the New Year with First Night Talbot 

First Night Talbot 2021 will celebrate the New Year in virtual style! Performances will take place throughout the evening directly to your home via live stream on December 31, culminating in the world-famous Crab Drop at 9 p.m. Enjoy a New Year’s Even dinner at one of Talbot County’s many restaurants then tune in to welcome 2022!


Come for the Magic of Christmas in St. Michaels

Events take place December 10-12, 2021. Check website for days and times of events.

Visit St. Michaels during the second weekend in December where 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 days are 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, shopping!


Fill the car with family and friends and take a drive to Oxford to meander by the beautiful historic neighborhood homes lit up for the holiday. At dusk, lighted crab pot trees twinkle at the end of almost every dock. Drive along the Strand to the small beach and take a moment to watch the lights glisten on the Tred Avon River. For an authentic Chesapeake Christmas, take a drive west to Tilghman Island to cross the Knapps Narrows Bridge into the quaint waterman village all dressed up for the holidays. Inns and restaurants abound in both destinations.

There’s more to get you in the holiday spirit in Talbot County!

Escape the hustle and bustle of the season in any or all of our charming towns. We know you’ll fall in love with our traditions while making new holiday traditions of your own.