Queen Anne’s County

11th Annual Car Show in Historic Stevensville — Saturday, November 7, 10 a.m. to 3 p.m.

Historic Stevensville will welcome classic car enthusiasts for a full day of beautiful automobiles, music, food trucks, local restaurants and family-friendly activities. Visitors can see competing cars, watch artistic activities and enjoy the atmosphere in the historic downtown district. Vehicle registration begins at 9 a.m., and general public admission is free. The event takes place along the streets of Historic Stevensville, Stevensville, MD 21666. For visitor information, Queen Anne’s County Tourism can be contacted at 410-604-2100.

8th Annual Holiday Bazaar — Saturday, November 21, 11 a.m. to 4 p.m.

The Kent Island Yacht Club is hosting its annual Holiday Bazaar, offering an opportunity to get started on holiday shopping while supporting local vendors. The event takes place in the club’s ballroom at 117 Yacht Club Drive, Chester, MD 21619. Visitors can enjoy a seasonal shopping event in a waterfront setting. For information, call 410-643-4101.

Holiday Concert and Art Market — Saturday, November 28, concert from 5 to 6 p.m.; market from 6 to 8 p.m.

Historic Christ Church will host an evening of live holiday music performed by local musicians, followed by an art market in the adjoining parish hall. The market will feature arts and crafts vendors, light refreshments, and opportunities for children to have their pictures taken with Santa and Mary Elf. Admission is free. The location is Historic Christ Church, 121 East Main Street, Stevensville, MD 21666.

Stevensville Holiday Tree Lighting — Saturday, November 28, 5 to 6:30 p.m.

The annual holiday lighting celebration at Pocket Park brings neighbors together for holiday music, caroling, dancing, seasonal characters and the lighting of the community tree. This free celebration takes place at Pocket Park, at Old Love Point Road and Cockey Lane, Stevensville, MD 21666. For further information, call 410-604-2100.

Centreville Tree Lighting — Wednesday, December 2, 7 p.m.

Centreville’s annual holiday tree lighting offers a chance for residents and visitors to gather downtown and welcome the Christmas season. The event is listed for Downtown Centreville, MD 21617. A specific street address has not yet been confirmed in the listing.

Centreville Holiday Parade — Friday, December 4, 6:30 p.m.

The Centreville Holiday Parade returns to downtown Centreville, bringing a festive community celebration to the county seat. Families can line the downtown streets to enjoy the holiday parade and seasonal atmosphere. The event is scheduled for Downtown Centreville, MD 21617, beginning at 6:30 p.m.

Kennard African American Cultural Heritage Center Free Tours — Saturday, December 5, 10 a.m. to 2 p.m.

The Kennard African American Cultural Heritage Center in Centreville will offer free public tours. Visitors can learn about African American education, community life and local history through museum exhibits and a resource library. The center occupies a former high school established in 1936 and named for education trailblazer Lucretia Kennard. The event takes place at the Kennard African American Cultural Heritage Center in Centreville, Maryland; the event listing did not provide a street address.

Kent County

Annual Kent County Holiday Parade — Friday, November 27, 5:30 to 8 p.m.

Downtown Chestertown will welcome the holiday season with marching bands, classic automobiles, decorated floats and an appearance by Santa Claus. The annual parade travels along High Street in Downtown Chestertown, MD 21620, and gives families a traditional small-town holiday outing. For information, call 443-480-1987.

Chestertown Art Walk — Saturday, November 28, 9 a.m. to 3 p.m.

Downtown Chestertown will feature artists, artisans, pop-up galleries and live music during this community arts event. Visitors can explore original artwork, connect with local makers and support the region’s creative community. The event takes place in Downtown Chestertown, MD 21620. For information, contact the Kent Cultural Alliance, 101 Spring Avenue, Chestertown, at 410-778-3700.

Caroline County

Stay Alert: Protect Your Money from Fraud and Scams — Tuesday, November 3, 6 to 7 p.m.

The Caroline County Public Library will host a free educational workshop to help residents recognize scams, phishing attempts and other financial fraud. Participants will learn practical ways to protect their personal information and money. The event is at the Federalsburg Branch Library, 123 Morris Avenue, Federalsburg, MD 21632. For information, call 410-754-8397.

Super Sticky Slime Night — Wednesday, November 4, 5:30 to 6:30 p.m.

Children ages 6 through 11 can enjoy a hands-on slime-making activity at the Caroline County Public Library’s Greensboro Branch. Participants will learn how to create slime using just three ingredients in this creative and entertaining children’s program. Registration is required. The event is at 101 Cedar Lane, Greensboro, MD 21639. Call 410-482-2173 for information.

Fall Seed Cleaning Workshop — Thursday, November 5, 6 to 7:30 p.m.

The Caroline County Public Library will present an educational workshop about harvesting and cleaning native plant seeds, with participation from Environmental Concern and the Wild Ones Delmarva Chapter. Attendees can learn techniques that help preserve and encourage native plants. The workshop is free, with registration required, at the Central Library, 100 Market Street, Denton, MD 21629. Call 410-479-1343.

Caroline County Council of Arts Main Street Banner Auction — Friday, November 13, 5 p.m.

The Caroline County Council of Arts will hold its fourth annual Main Street Banner Auction in Denton. This community arts event gives visitors an opportunity to support the local arts community through a special auction featuring the town’s banner art. The event is listed for Denton, MD 21629; the exact venue and ending time should be confirmed with the organizers.

Country Christmas Market — Saturday, November 28, 9 a.m. to 4 p.m.

A Country Christmas Market is scheduled at the Caroline County 4-H Club and Youth Park, 8230 Detour Road, Denton, MD 21629. The event offers a seasonal shopping opportunity at the county’s agricultural and community fairgrounds, with local vendors and holiday gift-shopping opportunities. The date, hours and venue are listed in a participating vendor’s holiday schedule.

Denton Holiday Parade and Lighting of the Green — Thursday, December 3, 6 p.m.

Denton will welcome the Christmas season with its annual holiday parade through downtown. Following the parade, the Denton Rotary Club will host the Lighting of the Green at the Caroline County Courthouse. Families can enjoy the festive procession and the traditional holiday lighting ceremony. The parade takes place along Market Street in Downtown Denton, MD 21629, beginning near the 200 block. For information, contact the Town of Denton at 410-479-2050.

Breakfast with Santa — Saturday, December 19, beginning at 8 a.m.

Caroline American Legion Post 29 will host Breakfast with Santa, offering families a chance to enjoy a holiday breakfast and a visit with Santa Claus. The event listing notes that breakfast is $10 per plate and that children on Santa’s nice list can receive small gifts. The event takes place at 9238 Legion Road, Denton, MD 21629.

Talbot County

OysterFest at the Chesapeake Bay Maritime Museum — Saturday, November 7, 10 a.m. to 4 p.m.

The Chesapeake Bay Maritime Museum will celebrate the region’s oyster heritage with a day of waterfront activities, including oyster dishes, live music, cooking competitions, boat rides and educational presentations. Family activities and demonstrations will highlight Chesapeake Bay traditions and the importance of oysters to the Bay’s environment and economy. The event is at 213 North Talbot Street, St. Michaels, MD 21663. Admission is ticketed. For information, call 410-745-2916.

Oxford Model Boat Show — Saturday, November 14, 10 a.m. to 4 p.m.

The Oxford Community Center will host a free model boat show featuring regional boat builders, exhibits and model boat sales. The family-friendly program includes indoor and outdoor displays and live music. Visitors can admire the craftsmanship behind miniature vessels while enjoying a day in historic Oxford. The location is Oxford Community Center, 200 Oxford Road, Oxford, MD 21654.

Eastern Shore Sea Glass and Coastal Arts Festival: Holiday Edition — Saturday, November 21, 10 a.m. to 4 p.m.

The Chesapeake Bay Maritime Museum will welcome artists and vendors from around the country for a special holiday edition of its popular Sea Glass Festival. Visitors can browse coastal artwork, jewelry, sea-glass creations and unique gifts while enjoying live music, glassblowing demonstrations and food vendors. The event is at 213 North Talbot Street, St. Michaels, MD 21663. Admission is ticketed. Contact the museum at 410-745-2916.

Easton Festival of Trees — Saturday, November 28 through Tuesday, December 1

The Festival of Trees returns to the Gold Room at the Tidewater Inn, 101 East Dover Street, Easton, MD 21601. This year’s theme is A Holiday to Remember. Visitors can explore dozens of beautifully decorated Christmas trees, enjoy seasonal entertainment and shop for festive gifts. The event benefits Talbot Hospice. Daily public hours vary and should be confirmed before visiting.

Easton Holiday Tree Lighting — Saturday, December 5, 5:30 p.m.

The Town of Easton will celebrate the holiday season with a community Christmas tree lighting in Thompson Park, Downtown Easton, MD 21601. Families can see Santa Claus help illuminate the tree and take holiday photographs before the evening parade.

Easton Holiday Parade — Saturday, December 5, 6:30 p.m.

Downtown Easton will come alive with decorated floats, marching bands, classic cars, holiday characters and an appearance by Santa and Mrs. Claus. The annual parade is one of the town’s most popular Christmas traditions. Visitors can enjoy the festivities along the streets of Downtown Easton, MD 21601.

Christmas in St. Michaels — Thursday, December 10 through Sunday, December 13

St. Michaels will celebrate four days of holiday activities, including the Christmas Marketplace, Sweet Shoppe, gingerbread displays, holiday shopping and community festivities. The celebration supports local nonprofit organizations and brings holiday traditions to the waterfront town. Activities take place at several locations throughout Historic St. Michaels, MD 21663, with individual schedules varying by event.

Christmas in St. Michaels Talbot Street Parade — Saturday, December 12, 10:30 a.m.

The annual Christmas parade will travel along Talbot Street, from Perry Cabin south to Seymour Avenue, St. Michaels, MD 21663. Families can enjoy marching bands, antique cars, fire engines, horses, holiday characters and the arrival of Santa and Mrs. Claus. The parade is free to attend and is scheduled to proceed rain or shine, except in dangerous lightning conditions.

Christmas in St. Michaels Tour of Homes — Saturday, December 12, 11 a.m. to 5 p.m., and Sunday, December 13, 11 a.m. to 4 p.m.

Visitors can explore historic homes decorated for the Christmas season during the annual St. Michaels Tour of Homes. Many of the residences date to the eighteenth and nineteenth centuries, offering a glimpse into the town’s maritime heritage and historic architecture. The self-guided tour includes transportation options between participating homes. Tickets are $35 in advance and $40 during the event. Ticket pickup is at Granite Lodge, St. Mary’s Square, St. Michaels, MD 21663.

Christmas in St. Michaels Lighted Boat Parade — Saturday, December 12, 6 p.m.

The waterfront will sparkle as decorated boats parade through St. Michaels Harbor, St. Michaels, MD 21663. This free public holiday event features illuminated vessels competing for recognition for their decorations. Spectators can watch from public viewing areas around the harbor.

Oxford Holiday Market — Friday, December 11 through Sunday, December 13

The Oxford Holiday Market will feature more than two dozen artisan merchants, specialty foods, gifts, holiday treats and family activities. Visitors can participate in the Elf Hunt, enjoy seasonal shopping and look for a Saturday visit from Santa Claus. The event takes place at the Oxford Community Center, 200 Oxford Road, Oxford, MD 21654. Daily market hours were not confirmed in the event listing.

Easton’s New Year’s Eve Crab Drop — Thursday, December 31, 9 p.m. and midnight

Easton will celebrate the arrival of 2027 with its traditional Crab Drop in Downtown Easton, in front of the Tidewater Inn, 101 East Dover Street, Easton, MD 21601. The festivities include an early countdown at 9 p.m. and another at midnight. Giving families and late-night revelers opportunities to welcome the New Year.