Ivory clapboard town house entry at blue hour with a copper canopy, bluestone steps, warm brass lantern, and an American holly.

Easton's Holiday Season Runs Nine Evenings, From the Festival of Trees Gala to the Parade

October 22, 2026

Downtown Easton's holiday season starts at 6 p.m. on Friday, November 27, with the Festival of Trees gala at the Tidewater Inn. It peaks eight days later at 6:30 p.m. on Saturday, December 5, when the parade steps off from Easton Elementary School. Out of those nine evenings, Wednesday, December 2, is the only one with nothing on this calendar.

That changes how to plan. The holiday parade, Shop Small Saturday and the Festival of Trees aren't spread through December. They sit side by side in one run that starts the day after Thanksgiving. Miss the first few days and you'll find the trees gone before the parade floats arrive. Plan it as one stretch and you can catch nearly everything without fighting the same crowd twice.

Friday to Tuesday, the Tidewater Inn holds the center of town

Talbot Hospice's Festival of Trees is in its 41st year, and the 2026 theme is "A Holiday to Remember." As the Talbot Spy put it, it's "held the first weekend after Thanksgiving." The Spy also reports that volunteers run the event under Friends of Hospice and that all proceeds go straight to Talbot Hospice, nearly $3.9 million so far. Dale Jafari chairs this year's festival and Gail Shorter is co-chair. Both have volunteered with the festival for years.

The dates moved one day earlier than last year. The 40th festival ran November 29 to December 2, 2025. This year's public days are Saturday, November 28, through Tuesday, December 1, in the Gold Room.

Here's the run in order:

  1. Preview Gala, Friday, Nov. 27, 6 to 8 p.m. Tickets are sold in advance only. Discover Easton lists them at $125 a person or $200 a couple.
  2. Santa 5K, Saturday, Nov. 28, 9 a.m. This one starts at Idlewild Park, away from downtown.
  3. Public festival days. Saturday 10 a.m. to 8 p.m., Sunday 11 a.m. to 8 p.m., Monday 10 a.m. to 8 p.m., and Tuesday 10 a.m. to 6 p.m.
  4. Santa's Workshop, Saturday afternoon. Children pose with Santa and the elves and make crafts. Published start times vary, so check the Festival of Trees site before you go.

Admission is $10 for adults and $5 for children ages 6 to 12. Children 5 and under get in free. Tuesday closes two hours earlier than the other days. For anyone who works a regular schedule, that makes Monday evening the last easy weeknight chance to see the trees.

What's inside, and why the small trees matter more than the big ones

The Gold Room holds 100 trees. Fifty are full-size display trees sponsored by individuals and businesses. The other fifty are decorated tabletop trees, 12 to 36 inches tall, and they're for sale. That second group is where practical holiday shopping comes in. If you're in an older downtown house with no room for a full tree, or you need a host gift, a decorated tree you can carry out the door is a real option. Pick one early in the run, before the best ones sell.

The Mistletoe Marketplace is back too. It carries curated items, including custom ornaments and notecards, plus wreaths and one-of-a-kind trees. Local artists, groups and musicians perform throughout the festival.

Shop Small Saturday lands on the festival's busiest day

Shop Small Saturday is November 28, the festival's first public day. Downtown's gift shopping and its biggest indoor event share the same Saturday. The Neighborhood Exchange at 25 E. Dover St. will be open 10 a.m. to 4 p.m. that day.

This is the first holiday season for a few downtown storefronts, so Saturday is also a good day to check them out:

  • Urban Country, 13 N. Harrison St. This family business sells furniture, rugs, lighting, home accessories and outdoor furnishings, and it offers interior-design services. Sascha Roth talked about the move to Easton with the Talbot Spy in September.
  • The Flour Shop, 115 N. Washington St. Bluepoint Hospitality's bakery opened in mid-August, according to The Daily Record. Executive Pastry Chef and Chocolatier Sarah Deale and Head Baker John Aversa run the bread and pastry program, according to the Star Democrat.
  • Bluepoint's retail wine shop. As of late September, The Daily Record said it was slated to open later in the fall.

Something is missing this year, too. The Costume Shop has closed after losing its space in the Brookletts Building, and its steward, Cece Davis, wrote about the loss in the Talbot Spy.

Wednesday is the one open night

The Festival of Trees closes at 6 p.m. on Tuesday, December 1. The next event in downtown's holiday run is Thursday evening at the Avalon. That leaves Wednesday, December 2, as the one free evening between Thanksgiving weekend and the parade. If you're hosting family through the first week of December, plan the quiet dinner at home for Wednesday.

Thursday to Saturday, the action moves to Washington and Harrison

The second half of the run moves out of the Tidewater Inn and spreads across downtown over three straight evenings.

Day Event Where Time
Thu., Dec. 3 Parsons Family Christmas Avalon's Stoltz Listening Room Doors 6:30 p.m., show 7 p.m., $30 before fees
Fri., Dec. 4 First Friday Gallery Walk Downtown galleries and shops Evening; Neighborhood Exchange open until 7 p.m.
Sat., Dec. 5 Santa arrives, then tree lighting Thompson Park 5:30 p.m., then 6 p.m.
Sat., Dec. 5 Easton Holiday Parade Glenwood Ave., Washington, Harrison and South streets 6:30 to 8 p.m.; street closures start at 6 p.m.

December's First Friday is the last Gallery Walk of the year, since the series runs April through December. The Neighborhood Exchange is staying open late for it.

Saturday night, block by block

Street closures start at 6 p.m. on December 5. That's the same time the tree is lit in Thompson Park, so anyone driving downtown for the parade needs to park before Santa throws the switch.

What's Up? Media laid out the route:

  • The parade steps off at Easton Elementary School and heads down Glenwood Avenue.
  • It turns onto North Washington Street and passes a panel of judges at the Talbot County courthouse.
  • It continues north on Washington, then loops onto North Harrison Street heading south.
  • From there it follows South Street and South Washington Street back to Glenwood Avenue.

Entries are judged in three categories: Best Nonprofit, Best Business and Best Marching Band. The courthouse is where the judging happens, so that stretch of North Washington is where entries tend to put on their best show. The loop also passes Urban Country on North Harrison and The Flour Shop on North Washington, the same storefronts that were new on Shop Small Saturday.

Santa's schedule ties the two parts of the evening together. What's Up advises arriving early to see him light the tree "before he rushes downtown to join the parade." In the same article, Tom Maglio, Events and Marketing Manager for the Easton Economic Development Corporation, describes the night this way:

"The great thing about this parade is that everyone in Easton comes together to enjoy it and be a part of the celebration."

The Festival of Trees opens on November 27 and the parade ends at 8 p.m. on December 5. Book gala tickets in advance, put Monday evening on the calendar for the trees, keep Wednesday free, and park before 6 p.m. on parade night.

I love seeing downtown Easton fill up for these nine nights, from the Gold Room trees to the judges' stand at the courthouse. If you're planning around the season, or you'd like to hear which downtown blocks and side streets feel most alive this time of year, Tracy Higgs Wagner would be happy to talk it through over coffee at The Flour Shop. Let's Connect.

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