Discover Easton
Bring your family and friends to Maryland's "Most Charming Small Town" during our annual
Holiday Events!
Scroll down for our 2026 events!
Holiday Events in Easton!
Talk to Rudolph
November 26 - December 21 | Talbot Town Shopping Center -
Monday through Saturday 10am - 9 pm, Sunday 10am - 6pm
Come see Rudolph and Santa at the Talbottown Shopping Center this holiday season.
Rudolph will listen to your holiday wishes from November 26 through December 21st!
Visit with Santa on Weekends: Sunday, Nov. 30, 12-2pm Saturday, Dec. 6, 3-5pm Friday, Dec. 12, 5-7pm Saturday, Dec. 13, 12-2pm Friday, Dec. 19, 5-7pm Saturday, Dec. 20, 12-2pm Sunday, Dec. 21, 12-2pm
Give Rudolph a call and share your holiday wish list so he can deliver it to Santa before Christmas!
Mon-Sat: 10 a.m. – 9 p.m.
Sun: 10 a.m. – 6 p.m.
EVFD Annual Holiday Train Garden
November 24 - December 25 | EVFD Fire Station (315 Aurora Park Drive)
The holiday train will fire up its engine to the delight of Easton area families. This festive tradition brings holiday treats, entertainment, and characters including Frosty the Snowman, Rudolph, and Santa’s elves.
Monday – Friday: 6 p.m. – 8 p.m.
Saturday & Sunday: 2 p.m. – 8 p.m.
Christmas Day: 11 a.m. – 2 p.m. & 4 p.m. – 8 p.m.
Candy Land 2024
Saturday, October 26 (One Day Only) 10 a.m. - 3:00 p.m. Rain or shine. Admission is FREE!
KIDS can navigate on a fun-filled journey playing games and winning prizes in the Peppermint Forest and Lollipop Woods.
Take some selfies in front of the Gingerbread House. Inside the VFW Great Hall, create Arts & Crafts, wander Candy Land Trail, and enjoy Story Time.
ADULTS can join the raffle of special themed baskets and explore handmade creations to purchase in our Candy Land Bazaar.
Easton VFW Post #5118, 355 Glebe Road, behind the Amish Market
FREE PARKING BEHIND THE VFW.
Presented by the Talbot County Women’s Club
Shop Small Saturday
November 28th
The unofficial start to the holiday shopping season in Easton begins with Shop Small Saturday! Support your independently-owned businesses that create jobs and help our local economy. Downtown businesses will showcase all of the latest styles and gifts for the holidays!
Holiday Tree lighting and pictures with Santa
December 5th | 5:30 p.m., Thompson Park
Make sure to come early downtown and catch Santa as he turns the lights on on our festive holiday tree in Thompson Park. Get a snap of the jolly man himself before he rushes downtown to host our traditional holiday parade. The Chamber of Commerce will have collection boxes at Thompson Park during the parade to collect for Toys for Tots.
Easton's Annual Holiday Parade
December 5th | 6:30 p.m.
Easton’s largest parade of the year includes some of the most creative and decked-out floats in town with dozens of organizations competing for the judge’s choice! Enjoy classic cars, marching bands, holiday characters, Mr. & Mrs. Claus, and more during this festive celebration!
Parade Signups Full, Registration is now Closed
Easton's Crab Crawl
The beloved New Years Eve tradition is back with a new face, new life, and a brand new crab!
As always, you can count down the New Year in Easton December 31st at 9 pm and 12 am in front of the Tidewater Inn on Harrison Street.
More Information Coming Soon
Festival of Trees
November 28 - December 1
A Holiday to Remember is the theme for the 2026 Festival of Trees which will be held in The Gold Room of The Tidewater Inn from Saturday, November 28 to Tuesday, December 1, 2026.
In a magical holiday setting, fifty beautifully decorated trees sponsored by individuals and businesses will be on display. In addition, fifty decorated trees ranging in size from 12” to 36” will be available for sale.
Throughout the festival, holiday entertainment will be performed by local artists, groups and musicians along with the sale of festive gifts.
Limited Edition Luminaries and a Poinsettia Sale are also available. See website for more information
Santa's Fun Run/Walk 5K
November 28 | 9 a.m.
Join Friends of Hospice for the Santa’s 5k Run/Walk, part of the annual Festival of Trees!
This fun run/walk starts at 9am at Idlewild Park in Easton, Maryland. Participants are encouraged to dress festive and hats and costumes encouraged (but not necessary) as we show our holiday spirit through Easton.
This race is pet friendly, bring your furry friends!
Santa’s 5k Run/Walk benefits Talbot Hospice through the Festival of Trees event, which is Talbot County’s largest fundraiser for Talbot Hospice. Run or walk in memory of a loved one, or to honor those who tirelessly care for our community’s needs each day.
Santa's Workshop
November 28 | 10 a.m. - 4 p.m.
This event returns, Saturday, November 28 and is sure to please the younger
holiday revelers as Santa makes a visit and his elves offer free activities.
For the admittance cost to the Festival of Trees, parents and guardians may enjoy
activities together with children of all ages from 10 am to 4pm on Saturday.
Make your way through the workshop, write a letter to Santa and drop it in
the mail, check out the train, paint an ornament, color a holiday picture, and
take a photo with Santa. Get into the holiday spirit!
Preview Gala by Festival of Trees
November 27 | 6 - 8 p.m.
The Preview Gala will again be a formal affair on Friday, November 27 with the kickoff of the Festival of Trees. From 6 to 8 p.m., guests will have the first opportunity to view 100 exquisitely trimmed trees of varying sizes. Tickets to the Preview Gala are available in advance only for $125 per person or $200 per couple.
Mistletoe Market
November 27 - December 1
Celebrate the season with a visit to the Mistletoe Market at the Festival of Trees. Discover a beautifully curated collection of holiday treasures, perfect for gifting or adding a touch of festive charm to your home.
From sparkling ornaments and whimsical felted mice to musical lanterns, colorful Santas, and glittering trees, each piece is chosen to capture the spirit of the season—and perhaps become a keepsake for years to come.
Be sure to explore a collection of wreaths and one-of-a-kind decorated trees, available for purchase in sizes ranging from 12 inches to 3 feet—each uniquely designed to bring a bit of holiday magic home.
Every purchase supports Talbot Hospice and the compassionate care they provide in our community.
The Mistletoe Market will open on Preview Night, Friday, November 27 and will run throughout the Festival.
Carols by Candlelight
November 29 | 5-7 p.m.
This free event will take place on Harrison Street in downtown Easton. This magical free holiday event for all families in Talbot County is back for our 6th year in 2025! Choral groups, bell ringers, and musicians will perform, and all spectators will receive a complimentary candle. Hot cocoa and holiday treats will be served as we spread holiday cheer in song. The celebration starts with a festive holiday marketplace filled with local craft and food vendors. Twinkling holiday accessories will be sold by Santa’s elves to help celebrate the beginning of the Christmas season in our picturesque town of Easton, a small town with a big holiday heart.
Starlight Shopping in Easton
December 4th, 11th & 18th | 5-7 p.m.
Join us for Starlight Shopping in downtown Easton on the first three Thursdays in December!
Stores will be open until 7:00 pm to meet all your holiday shopping needs, with live music adding to the festive atmosphere. The Hot Chocolate Trail returns this year, featuring restaurants and bars to enhance the seasonal stroll. Check often for more specials and events during Starlight Shopping in Easton.
Frosty's Village
December 12 | 5:00 p.m. - 7:30 p.m.
For All Seasons will host the fifth annual Frosty’s Holiday Village event on Friday, December 5, 2025, from 5 to 7:30 p.m. at the Anchor Church at 620 Goldsborough Street in Easton, with parking available at The Country School. This year’s event will feature over 50 inflatables and a larger resource tent featuring 12 resource partners who will provide fun games and important resources for families.
All activities will be free and include favorites such as professional photos with Frosty and friends, holiday crafts, Letters to Santa, Cascading Carlos the Juggler, face painting, complimentary cocoa and sweet winter treats, and a continuous showing of “Frosty’s Winter Wonderland” on the big screen. Participants are encouraged to pre-register for their photos with Frosty to avoid long wait times.
Easton Choral Arts presents "A Winter Rose"
December 5 : 7:30 pm & December 6: 4:00 pm
Amid the chill of winter, the rose has long symbolized beauty, memory, and hope. In this evocative holiday concert, Easton Choral Arts weaves together beloved carols, fresh arrangements, and such harmonies inspired by the flowers, plants, and greenery of the season. From the symbolic rose of Christ to the holly and ivy of English tradition, this program offers a rich tapestry of sacred and secular works, both timeless and new. Let the warmth of music bloom as we celebrate the gifts of nature, memory, and light in the heart of winter.
Bluepoint Holiday Market
December 6th - 24th
A curated selection of holiday essentials for gifting and entertaining, from ornaments to fine wine, in the historic Ebenezer Theater & adjacent Zach Gallery.
Plus complimentary photos with Santa! Saturday, Dec 7th from 2-6pm
Bluepoint Hospitality invites you to a free screening of the animated Christmas adventure Polar Express starring Tom Hanks on Sunday, December 8th at the Ebenezer at 12:00pm
Holiday Art & Craft Marketplace
December 1 - December 3 | Hours Vary
Located at the Waterfowl Building in downtown Easton. The marketplace will showcase fine arts and craft from local and regional artisans. Find one-of-a-kind, handcrafted gifts that make the perfect holiday presents.
Bluepoint Holiday Events
December 1&2, 7&8 | Hours Vary
Ebenezer Holiday Market: A curated selection of holiday essentials for gifting and entertaining, from ornaments to fine wine, in the historic Ebenezer Theater. Bring the family for photos with Santa Claus!
Children’s Storytime – 10:30 AM – Every Saturday at Flying Cloud books, children can enjoy a holiday tale
Holiday Carriage Rides
Times Vary - check website for availabilty
Enjoy carriage rides during the holiday season! Don’t miss the opportunity to see downtown Easton in classic fashion during the most wonderful time of the year.
Breakfast with Santa
December 8| Seating's at 9:00 a.m. & 9:30 a.m. Gold Ballroom, Tidewater Inn
Delight in a breakfast buffet tailored for both children and their parents, offering favorites like omelets, a waffle station, eggs benedict, and more + Bloody Mary’s and Mimosas for the adults. Here’s the surprise twist! Buddy the Elf will be joining us this year as the Master of Ceremonies.
For Reservations | Call Hunters’ Tavern 410-822-4034
The Avalon Foundation Presents - The Sound of Music
December 12 - 22| Doors open at 6:30p.m. / Matinee Doors 1:30p.m.
The Avalon Foundation presents the classic musical, The Sound of Music!
Come see The Sound of Music! It’s a family tradition and community experience wrapped up in a holiday celebration. Packed with a score of unforgettable songs (Do-Re-Mi, My Favorite Things, Edelweiss, Climb Every Mountain, The Sound of Music, Sixteen Going on Seventeen, and so many more!) The Sound of Music promises to delight audiences of all ages!
Join us for the Avalon Foundation’s annual holiday celebration and fundraiser starring over 130 of your friends and neighbors. All ticket proceeds go toward the Foundation’s year-round mission to provide diversified arts and educational programs that improve the quality of life here on the Eastern Shore.
2nd Annual Gingerbread Challenge
December 12| 6:00 p.m. - 8:00 p.m. Tidewater Inn
‘Tis the season for festive fun and friendly competition, and we’ve got an event that’s sure to sweeten your holiday spirit! Gather your friends and join us at the Tidewater Inn for our second annual Gingerbread Challenge! It’s an evening of spirited competition, delectable treats, and the chance to claim the coveted sweet champion title.
Reservations are available based on tables for your specified guest count—choose from tables accommodating 4, 5, or 6 guests. This is an adult-only event, ensuring an evening of laughter, creativity, and holiday merriment.
Skate with Santa
December 6 & 7 | Time varies; pre-registration required
Register now for Skate with Santa!
Santa will be taking a break from his busy schedule at the North Pole to visit the Talbot County Community Center and share holiday memories with the whole family! Kids will have an opportunity to sit on Santa’s lap to reveal their seasonal wishes and receive a special gift! Please bring your own camera to take a memorable photograph with Santa. Complimentary hot chocolate and cookies will be provided.
Pre-registration is required as Santa’s helpers need to maintain the quantity and quality of skates and gifts.
Home for the Holidays
December 7 & December 10
Easton Choral Arts Society presents its 2023 Holiday Concert, “Home for the Holidays”. Travel through the United States as this program takes the audience through a festive stylistic journey from Southern gospel to Midwestern folk to the Northeastern crooners and West Coast Hollywood flare. Even the islands from both the Atlantic and Pacific (Puerto Rico, Hawaii and more) will share their Christmas spirit. The program also features glorious works celebrating the sacred miracles of Hanukkah, the cultural principles of Kwanzaa, and the traditional sacred melodies of Christmas.
The chorus will sing the world premiere of the song “Santa Lucia”. Composed by ECAS’ Artistic Director, Alexis Renee Ward, it was influenced by the traditional “Festival of Lights” which was first observed along the banks of the Delaware River in the 1600s by settlers in New Sweden. Accompanying the chorus will be a professional guest instrumental ensemble of piano, percussion, and strings.
1st Annual Gingerbread Challenge
December 13 | 6:00PM-8PM
GINGERBREAD CHALLENGE
Join us on Wednesday, December 13th, from 6:00 PM to 8:00 PM in the Crystal Room for the Gingerbread Challenge.
Gather your friends for an incredible night of festive merriment and spirited competition. The Tidewater Inn is thrilled to present our first-ever Gingerbread Challenge, where teams will battle it out to claim the coveted sweet champion title. This adult-only event offers delectable appetizers and wine.
Elf the Musical
This modern-day holiday classic is sure to make everyone embrace their inner elf. After all, the best way to spread Christmas Cheer is singing loud for all to hear. Join us for the Avalon Foundation’s annual holiday celebration and fundraiser starring over 100 of your friends and neighbors. All ticket proceeds go toward the Foundation’s year-round mission to provide diversified arts and educational programs that improves the quality of life here on the Eastern Shore.