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Christmas in St. Michaels celebrates 40 years of holiday traditions and community giving
The Oaks Waterfront Hotel leads new sponsorship program supporting the Dec. 10-13 celebration.
Christmas in St. Michaels will celebrate its 40th anniversary Dec. 10-13, bringing four decades of holiday traditions and community giving to Maryland’s historic waterfront town. The milestone celebration invites visitors to enjoy decorated homes, gingerbread creations, holiday shopping, seasonal meals, and parades on land and water while supporting local nonprofit organizations.
The Oaks Waterfront Hotel leads the anniversary celebration as presenting sponsor, helping Christmas in St. Michaels launch its first major sponsorship program. The locally owned waterfront hotel near St. Michaels offers rooms, suites, cottages, dining, and a setting for weddings and special gatherings.
Platinum sponsors Higgins & Spencer and the Wildset Hotel & Ruse Restaurant join The Oaks in supporting the milestone celebration and its community mission.
Gold sponsors include the Chesapeake Bay Maritime Museum; Shore United Bank; Tracy Higgs Wagner, Realtor, Meredith Fine Properties; Guilford & Company; Carpenter Street Saloon; and Laura Carney, Senior Vice President, Sotheby’s International Realty. Community partners include Mid-Shore Community Foundation and Union United Methodist Church.
“Our local businesses have helped sustain Christmas in St. Michaels for decades,” said Christmas in St. Michaels Board President Pat Martin. “The Oaks Waterfront Hotel and our platinum and gold sponsors are building on that generosity with commitments that make a meaningful difference.”
“Their support reduces the time our volunteers spend seeking numerous smaller sponsorships and gives them more time to prepare a memorable weekend and support our beneficiaries,” Martin says. “We are grateful these partners have stepped forward for our 40th anniversary.”
The Chesapeake Bay Maritime Museum is one of this year’s gold sponsors. It will host Winter on the Chesapeake on Saturday, Dec. 12, from 1 to 7 p.m., bringing live music, festive food and drinks, holiday crafts, shopping, and waterfront fun to the anniversary weekend.
Guests can enjoy hot cocoa and s’mores around fire cauldrons, then gather along the museum’s waterfront to watch the Lighted Boat Parade at 6 p.m. Separate festival tickets and pricing are available at www.cbmm.org.
CBMM will offer free admission after 5 p.m. for boat parade viewing. Museum exhibitions will close, while the Museum Store, restrooms, and cocktail bar remain open until 7 p.m.
The holiday spirit extends throughout St. Michaels. The town’s retailers, historic inns, restaurants, and waterfront dining establishments all contribute to the celebration, welcoming visitors to shop, stay, dine, and enjoy the season between scheduled events.
The Gingerbread “House” Preview Cocktail Party opens the celebration Thursday, Dec. 10, from 5 to 7 p.m. at the St. Michaels Community Center. Guests will get an early look at the competition entries, enjoy food catered by Chef Mike, and bid on donated gingerbread creations in a silent auction benefiting Christmas in St. Michaels’ beneficiaries. Tickets for the adults-only event are $75 per person and available online.
The gingerbread display will welcome visitors free of charge Friday, Dec. 11, from 2 to 5 p.m.; Saturday, Dec. 12, from noon to 5 p.m.; and Sunday, Dec. 13, from 10 a.m. to 3 p.m. Visitors can vote for their favorite creation for the People’s Choice Award.
The Marketplace and Sweet Shoppe at Granite Lodge on St. Mary’s Square will offer artisan-crafted gifts, holiday decorations, baked goods, and specialty foods. Hours are noon to 3 p.m. Friday, 9 a.m. to 5 p.m. Saturday, and 10 a.m. to 3 p.m. Sunday. The Sweet Shoppe will also serve hot spiced cider, hot cocoa, locally roasted coffee, and cookies donated by chefs from local restaurants and businesses.
Saturday’s festivities begin with breakfast at St. Luke’s United Methodist Church, 304 S. Talbot St., from 7:30 to 10 a.m., with tickets sold at the door. Breakfast with Santa is also listed for children ages 4 to 9 at the St. Michaels Community Center from 8 to 10 a.m. Families can check the event website for updated reservation information.
The Talbot Street Parade begins at 10:30 a.m. on Saturday and travels south from the Inn at Perry Cabin to Seymour Avenue, with Santa and Mrs. Claus closing the procession. The parade route will be closed to vehicle traffic on Talbot Street from 10:15 a.m. to noon. Christ Church St. Michels is hosting a flute concert Saturday afternoon at 2:00 pm. This holiday music program will be presented by Dr. Thresa Bowers, flutist, and Dr. Cora Bruner, organist.
The Tour of Homes runs from 11 a.m. to 5 p.m. on Saturday and from 11 a.m. to 4 p.m. on Sunday. Guests can explore holiday-decorated homes and enjoy the historic streets connecting them. Tickets include one-time admission to each tour home, shuttle transportation, a tour guide brochure, and admission to the Chesapeake Bay Maritime Museum, Classic Motor Museum, and St. Michaels Museum on both days.
“Our town is beautifully decorated, and the spirit and warmth of the holidays are abundant during Christmas in St. Michaels,” Martin said. “Be sure to join us this December for one of Maryland’s longest-running home tours, showcasing a curated collection of beautifully decorated homes in our historic district.”
Tour tickets are $35 through Friday, Dec. 11, and $40 on Saturday and Sunday. Online sales close at noon Wednesday, Dec. 9. Advance tickets will also be sold at participating Talbot Street shops and at the Marketplace on Friday from noon to 3 p.m. Weekend ticket sales and pickup will take place at Granite Lodge, with Sunday ticket service ending at noon.
The Christ Church Christmas Bazaar will offer fresh greens, handmade greenery arrangements, seasonal décor, gifts, and homemade baked goods Saturday from 9 a.m. to 2 p.m. at the parish hall, 103 Willow St.
The Old-Fashioned Eastern Shore Christmas Dinner returns Saturday, Dec. 12, from 11 a.m. to 3 p.m., or until sold out, at Union United Methodist Church Parish Hall, 100 Fremont St. The meal features sliced roast turkey, Maryland fried oysters, homemade sides, and desserts. Dine-in and carryout meals are $25 per person, with tickets sold at the door.
The Lighted Boat Parade will bring decorated vessels through St. Michaels Harbor at 6 p.m. Saturday, offering a festive finish to a day of touring, shopping, and dining. Visitors can find parade information and viewing updates on the Christmas in St. Michaels website.
Sunday’s celebration concludes with a free holiday music program at 5 p.m. at St. Luke’s United Methodist Church. The Talbot County Workshop Choir, directed by Leroy Potter, will perform gospel music and traditional Christmas carols.
The 40th anniversary also celebrates the community generosity behind Christmas in St. Michaels. Since the all-volunteer organization began, sponsors and patrons have helped raise more than $1.7 million for local organizations supporting children, families, education, child development, and community enhancement.
Event schedules, ticket purchases, parade information, the 2026 collectors ornament, and beneficiary details are available at www.ChristmasinStMichaels.org.
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