Forty Years In, Christmas in St. Michaels Is Still Paying for the Day Care It Started With

When you buy a Tour of Homes ticket at The Christmas Shop on Talbot Street, where does the $35 go? The answer goes back to 1987. That year a group of volunteers saw that the community needed day care, a center was set up, and an annual weekend fundraiser began to support it. According to the Town of St. Michaels, money from the weekend's ticketed events goes directly to local nonprofits. That center is now the St. Michaels site of Critchlow Adkins Children's Centers. Christmas in St. Michaels calls it "the day care center originally funded and continually supported since 1987," and it is on the 2026 beneficiary list again.

This year's weekend, December 10 through 13, is the 40th. Across four decades the festival kept the job it started with. The parade, the gingerbread and the boats are how it raises money. The money goes to organizations that serve the Bay Hundred all year.

A fundraiser with a parade attached

The organization's mission is narrow and local: "to provide resources to help local non-profit groups enhance the quality of life for the residents of the Bay Hundred community." By its own count, the weekend has raised more than $1,700,000 for local nonprofits since that first day care effort.

The day care isn't the only lasting result. Bay Hundred Community Pool is on the festival's list of past beneficiaries, and its support helped underwrite the pool's construction and has continued since. If you swim there in summer or drop a child at Critchlow Adkins on a weekday, you are using something the December weekend helped pay for.

The 2026 beneficiary list reads like a map of the Bay Hundred

The 2026 beneficiaries are the clearest evidence that the festival still works the way it did in 1987. Almost every name is an organization you would recognize from a walk through town.

The St. Michaels Fire Works Fund and the Farmers Market are on the list. So is Tilghman's fire department, along with a Royal Oak church. The geography is the whole Bay Hundred, well beyond Talbot Street.

What each part of the weekend raises money for

Since the beneficiaries are the reason the weekend exists, it helps to know which events cost money and which are free. These are the 2026 details the festival has posted.

1. Gingerbread Preview Cocktail Party. Adult tickets are $75 for this event at St. Michaels Community Center. Competition winners are announced there, and a silent auction benefits the festival's beneficiaries.
2. Gingerbread display. The public display at the Community Center is free. The competition has seven categories, plus awards for the best Eastern Shore depiction and People's Choice.
3. Marketplace & Sweet Shoppe. It's back at Granite Lodge on St. Mary's Square with artisan gifts, food items, baked goods, hot spiced cider, cocoa and locally roasted coffee.
4. Tour of Homes. Hours are Saturday 11 a.m. to 5 p.m. and Sunday 11 a.m. to 4 p.m. The ticket covers the tour homes, the shuttle, a brochure, and admission on both days to the Chesapeake Bay Maritime Museum, the Classic Motor Museum and the St. Michaels Museum.
5. The 2026 collectors' ornament. At $32, it's the 23rd in the series and marks the 40th anniversary. It's based on artwork by local artist Naomi Clark.

Tour of Homes tickets are $35 through Friday, December 11, and $40 on the Saturday and Sunday of the tour. Online sales close at noon on Wednesday, December 9. In person, tickets are planned at The Christmas Shop, Chesapeake Trading Company and Charisma, and Granite Lodge on St. Mary's Square handles pickup and sales over the weekend. Eye On Annapolis reported the same $35 and $40 prices in 2025, so the 40th year didn't bring an increase.

The museum admissions in that ticket matter here. The Classic Motor Museum and the St. Michaels Museum at St. Mary's Square are both on the beneficiary list, so a tour ticket also brings visitors through the doors of two of the organizations it helps fund.

The festival also lists Breakfast with Santa, holiday meals, the Christ Church Bazaar and Sunday music for the weekend. Times and tickets for each are posted on its events page.

The weeks before belong to other organizers

The St. Michaels Business Association and the Chesapeake Bay Maritime Museum each run their own events in the weeks before the 40th weekend, and the money from those stays with the businesses and the museum that hold them. Here's what is still ahead as of publish day.

At the Sea Glass Festival, CBMM's October 28 announcement lists Chris Sacks, Levi Stephens, Alison Thoms and Anna Burgess among the performers, and sea glass expert Mary McCarthy leading activities. Online admission is $22 for adults, $19 for seniors and students, $10 for military and $9 for ages 6 to 17, and children 5 and under get in free.

Taste of St. Michaels brings together St. Michaels Salt Co., San Miguels, The Galley, Simpatico, Old Brick Inn, Olive Branch, Corah's Corner, Ava's Pizzeria & Wine Bar, Talbot St. Tavern, St. Michaels Winery and Gina's Cafe. Five days later, on Thursday, December 3, the SMBA's Winter Fest returns for four days. Each downtown business hosts its own dinner specials, shopping offers and holiday surprises, with individual offers to be announced.

These events fill the calendar before the festival. They come from different groups, and the money goes to different places.

Saturday, December 12, from morning to the harbor

The festival's Saturday is the busiest day of the season. On that one day, Christmas in St. Michaels and CBMM share the waterfront.

1. Morning. The free Talbot Street Parade steps off at 10:30 a.m. and runs south from the Inn at Perry Cabin to Seymour Avenue. Talbot Street is closed to vehicles from 10:15 a.m. to noon, so plan errands that need the main street around those hours.
2. 11 a.m. The Tour of Homes opens and runs until 5 p.m.
3. 1 p.m. CBMM opens Winter on the Chesapeake on its campus. It runs until 7 p.m. with live music, food and drink, horse-drawn carriage rides, Museum Store shopping, crafts, hot cocoa and s'mores. Online tickets are $22 for adults, $19 for seniors and students, $10 for military and $9 for youth. Prices are $2 higher at the door, and members get discounts.
4. 5 p.m. CBMM admission is free for boat-parade viewing. The exhibitions close, but the Museum Store, restrooms and cocktail bar stay open until 7 p.m.
5. 6 p.m. The Lighted Boat Parade starts. Boats come from Miles River Yacht Club into St. Michaels Harbor and make a circuit past the crowds on shore, and the route passes the CBMM campus.

The boat parade is a judged competition. Winners get bragging rights and a feature on the festival's website, and boat owners who want to enter contact the organizers so the parade chair can follow up. CBMM's Old Point took first place in 2025, Working Girl came second, Charmed was third, Glacier Bay fourth, and the St. Michaels Fire Department's entry fifth.

The 40th ornament goes back to the water

The festival has drawn on the harbor for this year's keepsake as well. The 40th-anniversary ornament shows Working Girl, the boat from last year's parade, in Naomi Clark's artwork. Like all the festival's ornaments and products, its proceeds go directly to local nonprofits. At $32, it's the smallest purchase on the weekend's list, and it supports the same beneficiaries as the $75 preview party.

If you're planning the 40th weekend around friends, family or guests coming to town, I'm always glad to help with the details, from Talbot Street closure times to the harbor at 6 p.m. Reach out to Tracy Higgs Wagner and let's connect before December 10.