Christmas in St. Michaels invites you to celebrate the season at one of the town’s most anticipated holiday events—the Gingerbread Competition Preview Cocktail Party and Silent Auction—held Thursday, Dec. 11, from 5 to 7 p.m. at the St. Michaels Community Center, located at 103 Railroad Avenue.

This festive evening features handcrafted cocktails, passed appetizers by Chef Mike Willis, and the first viewing of this year’s whimsical gingerbread creations. Each edible masterpiece, designed by talented local bakers and artists, will be showcased before being opened to the public during the Christmas in St. Michaels weekend.

“The cocktail party is truly the highlight of the holiday season,” said Pat Martin, chair of Christmas in St. Michaels. “It’s a joyful celebration of community, creativity, and generosity—and it sold out quickly for our inaugural event last year.”

Guests can also participate in a silent auction to bid on their favorite gingerbread houses, with proceeds benefiting local nonprofits supported by Christmas in St. Michaels.

“Your bid helps make a difference right here in our community,” said Amy Horne, executive director of the St. Michaels Community Center. “This event combines holiday cheer with the spirit of giving back, which is what the season is all about.”

Tickets are $75 per guest and limited to 120 attendees. Advance registration is required and available online at www.christmasinstmichaels.org/events.

Enter the Gingerbread Competition
While the gala is limited to adults, community members of all ages are encouraged to enter their own gingerbread creations for the competition. Entries will be judged on creativity, craftsmanship, and presentation, with winners announced during the cocktail party. Details and registration are available on the website or by contacting Amy DeWitt at [email protected].

Drop-off hours for gingerbread entries will be Tuesday, December 9, from 3:00 to 7:00 p.m., and Wednesday, December 10, from 9:00 a.m. to 1:00 p.m.

The gingerbread houses will be on public display at the St. Michaels Community Center from Friday, Dec. 12, through Sunday, Dec. 14, as part of the Christmas in St. Michaels festivities. Friday viewing hours will run from 2 to 5 p.m. to accommodate the center’s food programs.

Snap a Photo at Santa’s Workshop, Breakfast with Santa

On Saturday, Dec. 13, SMCC, in partnership with S.M.Y.L.E., will host Santa’s Workshop, featuring a Foto Berry photo booth for families to capture special holiday memories.

During the festive weekend of Christmas in St. Michaels, guests can immerse themselves in a delightful blend of holiday cheer, tradition, and community celebration throughout the historic waterfront town.

A family-favorite event includes Saturday’s Breakfast with Santa for children ages 4 to 9 years old, which takes place from 8-10:00 a.m. at the waterfront Foxy’s Harbor Grille, with limited $10 tickets available for advance purchase.

Highlights include historic homes decked out for a special Tour of Homes, lively parades both on land and water, holiday meals, and the popular Marketplace & Sweet Shoppe, where artisan gifts, treats, and seasonal décor await shoppers.

Since 1987, Christmas in St. Michaels has brought holiday joy to the Eastern Shore while raising more than $1.7 million to benefit organizations that strengthen the St. Michaels and surrounding communities year-round. For more information, including event details and online purchases, visit www.christmasinstmichaels.org

Families are invited to make memories at one of the region’s most beloved Christmas traditions: Breakfast with Santa, from 8–10 a.m. Saturday, Dec. 13, at the waterfront Foxy’s Harbor Grille in St. Michaels. Limited tickets are just $10 per child, with advance purchase strongly recommended.

 

The event is open to children ages 4–9 and offers a festive morning of food, fun, and holiday cheer with Santa himself.

 

The breakfast is part of Christmas in St. Michaels, which returns for its 39th year of holiday celebrations Dec. 11–14 in the heart of historic, waterfront St. Michaels. The weekend features favorite annual events including the Tour of Homes, Marketplace and Sweet Shoppe, Talbot Street Parade, and a Lighted Boat Parade.

 

Festivities begin Thursday, Dec. 11, with the Gingerbread House Preview Cocktail Party at 5 p.m. at the St. Michaels Community Center. Tickets are $75 and available in advance online. Gingerbread houses will then be on public display beginning Friday, Dec. 12, at 2 p.m., with visitors encouraged to vote for their favorite designs throughout the weekend.

 

Saturday’s events continue after Breakfast with Santa with the Talbot Street Parade at 10:30 a.m., which includes Santa waving to parade-goers. Guests can attend the Tour of Homes and enjoy a full day of shopping, dining, and live music across town. The Lighted Boat Parade along St. Michaels Harbor caps off the evening from 6–7 p.m.

The Tour of Homes runs Saturday and Sunday, with $35 advance tickets available online or $40 in person at The Marketplace and Sweet Shoppes during the weekend. Each ticket includes one-time admission to all tour homes, a detailed tour guide booklet, and complimentary admission to the Chesapeake Bay Maritime Museum, Classic Motor Museum, and the St. Michaels Museum at St. Mary’s Square.

Holiday dining favorites return as well, including the Old-Fashioned Eastern Shore Christmas Dinner from 11 a.m.–3 p.m. Saturday, Dec. 13, at Union United Parish Hall. Dinners include sliced roast turkey, Maryland fried oysters, and a variety of sides and desserts for $25 per person, available for dine-in or carry-out.

The Marketplace and Sweet Shoppe at St. Mary’s Square’s Granite Lodge opens at noon Friday, Dec. 12, with artisan-crafted gifts and local treats available through Sunday afternoon.

“Our town is beautifully decorated, and the spirit and warmth of the holidays are abundant during Christmas in St. Michaels,” said Pat Martin, board president of Christmas in St. Michaels. “Join us this December for one of Maryland’s longest-running holiday traditions.”

Since its founding, Christmas in St. Michaels has raised more than $1.7 million to support local organizations serving children, families, and the community.

For Breakfast with Santa tickets, event schedules, and updates, visit christmasinstmichaels.org.

Christmas in St. Michaels has recently unveiled its 2025 Christmas in St. Michaels Limited Edition Collector’s Ornament, with the 22nd in the series depicting the historic Teetotum Building at the St. Michaels Museum at St. Mary’s Square. The design is based on original artwork by local artist Maggii Sarfaty.

“The Teetotum is one of the most recognizable landmarks in town, and this year’s ornament lets us share that piece of history with everyone who loves St. Michaels,” said Christmas in St. Michaels Chair Pat Martin. “This ornament celebrates its story of resilience, community, and how our town preserves its past.”

The Teetotum Building dates to the 1850s and is the central of three structures comprising the St. Michaels Museum. The unusual name comes from its roof design, which resembled a gambling spinning top called a “teetotum.” Some locals also referred to it as the “teetotal” because of its perfectly square footprint.

Around 1940, the building was remodeled into a single room, where local barber Eugene Harrison operated “Gene’s Barber Shop” from 1937 to 1968. Today, his barber’s chair and shoeshine stand remain in their original places. The building was moved to its current site at East Chestnut Street and St. Mary’s Square in 1968 and given to the museum by the bank.

“Museum exhibits in the Teetotum tell some of our most important stories—from daily life on St. Mary’s Square, the original heart of the town, to the British attacks of 1813, and even the life and times of Frederick Douglass,” Martin said. “That history is something we want to keep alive, and this ornament is a keepsake reminder of that heritage.”

The boxed ornament will be available at select local retail shops and during the Christmas in St. Michaels Marketplace and Sweet Shoppe. Online purchases for all St. Michaels Limited Edition Collector’s Ornaments can be made at christmasinstmichaels.org/ornament.

Since the all-volunteer organization’s beginnings, sponsors and patrons of Christmas in St. Michaels have helped raise more than $1.7 million to support local children and adults through education, child development, and community programs.

For more information, including event details and online purchases, please visit christmasinstmichaels.org.

Gingerbread “House” Preview Cocktail Party kicks off weekend of events on Thursday evening.

Experience holiday joy in the heart of historic waterfront St. Michaels, Maryland, with Christmas in St. Michaels hosting a full weekend of events and celebrations from December 11-14.

This 39^th year of the event is highlighted by the return of the Gingerbread Contest, with a Gingerbread House Preview Cocktail Party kicking off the weekend of events on Thursday, December 11, beginning at 5 p.m. The preview party takes place at the St. Michaels Community Center. Limited $75 tickets are available for advanced purchase online.

These gingerbread houses will be on display at the St. Michaels Community Center beginning at 2:00 p.m. on Friday and continuing during select hours through Sunday. Viewers will be invited to vote for their favorite designs to help determine this year’s winners.

The weekend of festivities is highlighted by crowd favorites like the Tour of Homes, Saturday’s Breakfast with Santa, and the Marketplace and Sweet Shoppe, along with two parades on Saturday – the Talbot Street Parade at 10:30 a.m. and the Lighted Boat Parade along St. Michaels Harbor at 6 p.m., with plenty of places to watch the boats passing by.

The Tour of Homes runs on Saturday and Sunday, with $35 advanced tickets available online or for purchase at The Marketplace and Sweet Shoppes throughout the weekend.

You can also start your Saturday with a holiday continental breakfast at St. Luke’s Methodist Church, enjoy a delicious Old-Fashioned Eastern Shore Christmas Dinner later at Union United Parish Hall, and take in music out and about in this waterfront, vacation-friendly town. The events are ticketed, with limited seating and more online.

The Marketplace and Sweet Shoppe are located at St. Mary’s Square’s Granite Lodge and open at noon on Friday, Dec. 12, with select hours through Sunday, Dec. 14 at 3 p.m. Shoppers will find one-of-a-kind, artisan-crafted items, and culinary delights available only during this weekend event.

Music will mix with the brackish air of this historic harbor-front town on Sunday, Dec. 14, including gospel and traditional Christmas music from the Mid-Shore Voices of the Covenant Gospel Choir at Union United Methodist Church on Sunday, beginning at 5 p.m.

Family-favorite events include Saturday’s Breakfast with Santa for children ages 4 to 9 years old, which takes place from 8-10:00 a.m. at the waterfront Foxy’s Harbor Grille, with limited $10 tickets available for online purchasing.

The 10:30 a.m. Talbot Street Parade and the beginning of the Tour of Homes are wonderful mid-day events, with the Lighted Boat Parade along St. Michaels Harbor from 6 to 7:00 p.m. Parade routes, event details, online tickets, and more are at christmasinstmichaels.org.

“Our town is beautifully decorated, and the spirit and warmth of the holidays are abundant during Christmas in St. Michaels,” says Christmas in St. Michaels Board President Pat Martin. “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.”

The Tour of Homes runs on Saturday and Sunday, with $35 advanced tickets available online, or for $40 purchased at The Marketplace and Sweet Shoppes throughout the weekend.

A Tour of Homes ticket includes one-time admission to all tour homes; a detailed tour guide booklet with local information and other major St. Michaels landmark descriptions; and free admission to the Chesapeake Bay Maritime Museum, the Classic Motor Museum, and the St. Michaels Museum at St. Mary’s Square for Saturday and Sunday.

Christmas in St. Michaels’ Old Fashioned Eastern Shore Christmas Dinner takes place on Saturday, Dec. 13, starting at 11:00 a.m. and lasting until 3:00 p.m., or when the meals are sold out.

Dinners include sliced roast turkey, Maryland fried oysters, and a large assortment of sides and desserts. The event will be held at the Union United Parish Hall on Fremont Street in St. Michaels, with dine-in and carry-out dinners available at $25 per person, with tickets sold at the door on the day of the event.

Since the all-volunteer organization’s beginnings, sponsors and patrons of Christmas in St. Michaels have helped raise more than $1.7M in support of local children and adults served by family-focused, education, child development, and community enhancement organizations. Event updates, online ticket and ornament purchases, and more about Christmas in St. Michaels are at christmasinstmichaels.org.

Celebrate the season with the 38th annual Christmas in St. Michaels, a cherished holiday tradition in the heart of this historic waterfront town. From December 13- 15, enjoy a weekend packed with festive activities, including parades, shopping, music, and the highly anticipated Tour of Homes.

The weekend features beloved events like the Talbot Street Parade at 10:30 a.m. Saturday, followed by the enchanting Lighted Boat Parade at 6 p.m. Other highlights include Breakfast with Santa at Foxy’s Harbor Grille, the Old-Fashioned Eastern Shore Christmas Dinner, and the Marketplace and Sweet Shoppe, located at St. Mary’s Square. Proceeds from Marketplace sales benefit local nonprofits.

The Tour of Homes, showcasing exquisitely decorated residences, runs Saturday and Sunday. Tickets are $35 in advance or $40 during the event and include a detailed guidebook, transportation to countryside homes, and access to local museums.

“We’re excited to welcome visitors to our beautifully decorated town to share the spirit of the season,” said Christmas in St. Michaels Board President Pat Martin. “This event brings together the community and supports organizations that make a difference in the lives of our residents.”

Christmas in St. Michaels has raised more than $1.7 million for local nonprofits over its nearly four decades. For tickets, event schedules, and updates, visit christmasinstmichaels.org.

Bakers and pastry chefs of all ages and talent levels are encouraged to get their gingerbread house games on with the return of the Christmas in St. Michaels Gingerbread House competition this December and a purse totaling $2,000 in prizes up for grabs.

The competition is an important component of the fundraising the all-volunteer organization achieves with the annual event, with the creations highlighted and on display at the Gingerbread “House” Preview Cocktail Party at the Woman’s Club of St. Michaels on Thursday, December 12 beginning at 5 p.m.

“We are encouraging participants to donate their creations for our silent auction, to be held the evening of the cocktail party,” says this year’s Gingerbread House Competition Co-Chair Michele Lowe. “All auction proceeds support the beneficiaries of Christmas in St. Michaels.”

Entrants can pick their category for participation, which includes master chefs and caterers, adults, young adults, children, children with adults, kit-made houses, and non-profit organizations. Participation is free, with pre-registration needed at www.christmasinstmichaels.org/events.

The 2024 Christmas in St. Michaels Collectors Ornament has also been announced and is the 21st in the series. This year’s ornament depicts the Chesapeake deadrise workboat with its crew and a friendly canine companion. The image was provided by St. Michaels artist Sherry Smith.

The boxed ornament is available for purchase at select local retail shops and the weekend-long Christmas in St. Michaels Marketplace and Sweet Shoppe. Online purchases can be made at www.christmasinstmichaels.org/ornament.

The deadrise workboat has been a staple among Chesapeake watermen for decades. “Deadrise” refers to the almost flat, V-shaped hull that provides a shallow draft to accommodate the waters in creeks and rivers of the Eastern Shore. Boats range from 25-45 feet in length and are powered by large, inboard 4 or 6-cylinder engines, usually diesel-fueled.

These wooden workboats typically have a forward housing or small cabin and a large open stern area that can accommodate various tools of the trade including nets, oyster tongs, wire mesh crab pots, bushel baskets to hold the catch, and myriad other bits and pieces of the watermen’s equipment.

The shallow sides of the craft provide easy access to the water, a necessity for trot-lining for crabs and maneuvering oyster tongs. A wooden or canvas roof protects watermen from the sun although in other seasons, a large metal clamming device is attached near the stern and the roof is removed.

Workboats typically sport women’s names on the transom or bow, paying tribute to wives and daughters. Others, such as the one in this ornament, refer to the town, river, or creek the boat calls home port.

“It is typical to see dozens of these deadrise workboats plying the waters of the Eastern Shore in the wee hours of the morning as they seek the day’s catch, returning to the pier in the early afternoon to get their catch to market,” says Christmas in St. Michaels Chair Pat Martin. “We’re honored to add this limited-edition ornament to our collection to pay tribute to watermen and their boats in the St. Michaels area and the Chesapeake Bay region at large.”

Since the all-volunteer organization’s beginnings, sponsors and patrons of Christmas in St. Michaels have helped raise more than $1.7M in support of local children and adults served by family-focused, education and child development, and community enhancement organizations.

Event details, online ticket and ornament purchases, and more about Christmas in St. Michaels are at christmasinstmichaels.org.