Queen Anne’s County

Kent Narrows Boat Expo — Friday through Sunday weekends, October 10–11, October 16–18, and October 23–25, 2026, generally 10 a.m. to 4 p.m.
The Kent Narrows Boat Expo runs along the connected docks from Fisherman’s Village at the Crab Deck and Hyatt Place in Kent Narrows / Grasonville. It is a free public boat-browsing event featuring boats from Knot 10 Yacht Sales and is a good fit for people who like being around the water, boats, and the Kent Narrows waterfront scene. Queen Anne’s County Tourism lists the event as running across three October weekends. Visit Queen Anne’s County

Kent Island Heritage Center Open for Tours — Saturdays, October 10, 17, 24, and 31, 2026, noon to 4 p.m.
The Kent Island Heritage Center is open for Saturday tours at 310 Love Point Road, Stevensville, MD. This is a simple, history-focused stop for visitors who want to learn more about Kent Island’s long local story, with exhibits inside the renovated 1870 Queen Anne’s County School House. Visit Queen Anne’s County

Sudlersville Base Ball Showdown & Picnic — Saturday, October 10, 2026, 1 p.m.
This public community event takes place at Sudlersville Park, Sudlersville, MD. It celebrates old-time base ball as it was played in the 1860s, with vintage uniforms, old-style equipment, and a nod to Sudlersville baseball legend Jimmie Foxx. It should work well as a light local-history and family event. Visit Queen Anne’s County

Centreville Farmers’ Market — Sundays, November 1, 8, 15, 22, 29, and December 6, 2026, 9 a.m. to 1 p.m.
The Centreville Farmers’ Market is held on Lawyers Row in Centreville, MD, with local produce and handmade goods. It is a good recurring public event for a community calendar, especially for listeners looking for a low-key Sunday outing. Visit Queen Anne’s County

11th Annual Car Show in Historic Stevensville — Saturday, November 7, 2026, public hours 10 a.m. to 3 p.m.
Classic cars line the streets of Historic Stevensville, MD, with music, food trucks, local eateries, and family-friendly activities. The Queen Anne’s County listing says car entry begins as early as 9 a.m., with the public welcome from 10 a.m. to 3 p.m. Visit Queen Anne’s County

Holiday Concert & Art Market — Saturday, November 28, 2026, 5 p.m. to 6:30 p.m.
This free holiday event is at Historic Christ Church, 121 East Main Street, Stevensville, MD. The evening starts with live local holiday music in the church, followed by an art market with arts and crafts vendors, light finger food, and a chance for children to visit with Santa and Mary Elf. Visit Queen Anne’s County

Queen Anne’s County First Saturdays: Wright’s Chance, Tucker House, QAC Centre for the Arts, and Kennard African American Cultural Heritage Center — Saturday, December 5, 2026, 10 a.m. to 2 p.m.
Queen Anne’s County Tourism lists several Centreville First Saturday tour stops on December 5, including historic house museums, the Centre for the Arts, and the Kennard African American Cultural Heritage Center. These are public history and heritage stops in Centreville, MD, and they make a good daytime listing for families and history-minded visitors. Visit Queen Anne’s County

Kent County

Rock Hall FallFest — Saturday, October 10, 2026, 10 a.m. to 4 p.m.
FallFest takes place in Rock Hall, MD, with general parking listed at 21125 Sharp Street, Rock Hall, MD. The festival celebrates Eastern Shore heritage with oysters, live music, handmade craft vendors, regional food vendors, and free children’s activities. It is one of the strongest Kent County public events for the period. Rock Hall Fall Fest

Caroline County

Eastern Shore Bluegrass Event — Sunday, October 11, 2026, 1 p.m.
Downtown Denton lists this event in Denton, MD, describing it as an American Legion Post 29 event showcasing regional bluegrass bands. The general American Legion Post 29 address commonly associated with Downtown Denton listings is 9238 Legion Road, Denton, MD 21629. Downtown Denton

Boo & Glue Story Time — Saturday, October 17, 2026
This Caroline County Public Library event is listed through the Caroline County Chamber calendar as a Denton library program. It is a public children’s event with a Halloween-season theme, and it fits the family/community category rather than a bar or theatre event. www.carolinechamber.org

Denton Halloween Parade — Thursday, October 29, 2026, 5:30 p.m. to 6:30 p.m.
The Town of Denton road-closure page lists the Halloween Parade on Market Street in Downtown Denton, MD, with Market Street closed from the 900 block to the 300 block during the parade. It is hosted by Downtown Denton Main Street and should be a good family-oriented seasonal listing. Denton Maryland

Movie of the Month — Tuesday, November 10, 2026, 5:30 p.m. to 7:30 p.m.
Caroline County Public Library lists this all-ages movie program at the Federalsburg Branch, Federalsburg Large Meeting Room, Federalsburg, MD. The library describes it as a monthly movie night where families and community members can gather in a calm setting. Caroline County Public Library

Tween Zone: Stellar Spaces — Thursday, November 12, 2026, 5:30 p.m. to 7 p.m.
This children’s library program is at the Central Branch Denton, Large Meeting Room, Denton, MD. It is designed for ages 6 to 11 and includes a constellation craft, a rocket pageant, and treats, making it a good public family listing. Caroline County Public Library

Denton Holiday Parade and Lighting of the Green — Thursday, December 3, 2026, 6 p.m.
Downtown Denton lists the 2026 Holiday Parade and Lighting of the Green for Downtown Denton, MD, beginning at 6 p.m. The Town of Denton listing describes it as a festive family parade downtown. The Town of Denton contact shown on the event page is 4 North 2nd Street, Denton, MD 21629, phone 410-479-2050. Downtown Denton

Breakfast with Santa at Caroline Post 29 — Saturday, December 19, 2026, 8 a.m.
Downtown Denton lists Breakfast with Santa at Caroline Post 29 in Denton, MD. The listing notes a $10 plate and small gifts for children on Santa’s nice list, making it a simple holiday family event for the Caroline County section. Downtown Denton

Talbot County

Historic Walking Tours — Saturday, October 17, 2026, 11 a.m. and noon
The Talbot Historical Society hosts historic walking tours from 25 South Washington Street, Easton, MD. The Easton calendar describes the tours as a look at the people, stories, and events that shaped Easton and Talbot County from the mid-18th century forward. Reservations are listed through 410-822-0773 or kaylaw@talbothistory.org. Easton, Maryland

Gather ’Round! Community Dance — Saturday, October 17, 2026, 4:30 p.m. to 6:30 p.m.
Discover Easton lists this community dance at 10028 Ocean Gateway, Easton, MD 21601. It is a public community event and a good non-bar, non-theatre listing for people looking for something social and active. Discover Easton, Maryland

St. Michaels Jack Russell Races — Sunday, October 18, 2026, 9:30 a.m. to 12:30 p.m.
The St. Michaels Business Association lists the Jack Russell Races at the St. Michaels Inn, St. Michaels, MD. The event welcomes dogs big and small and supports local animal charities, including Talbot Humane, Baywater Animal Rescue, and Caroline County Humane Society. St. Michaels Business Association

Outdoor Movie Night: A Nightmare on Elm Street — Friday, October 30, 2026, 8 p.m. to 10 p.m.
Discover Easton lists this outdoor movie night at The Ivy Café, 12 West Dover Street, Easton, MD. Since it is a public outdoor movie event rather than a theatre listing, it fits the calendar filters, though the title is more Halloween-oriented and probably best for adults or older teens. Discover Easton, Maryland

Festival of Trees — Saturday, November 28 through Tuesday, December 1, 2026
Discover Easton’s holiday page lists the 2026 Festival of Trees at The Gold Room of the Tidewater Inn, Easton, MD. The 2026 theme is listed as “A Holiday to Remember,” and this is one of Easton’s larger holiday-season public attractions. Discover Easton, Maryland

Winter Fest in St. Michaels — Thursday, December 3 through Sunday, December 6, 2026
Winter Fest takes place throughout Downtown St. Michaels, MD, with shopping, dining, holiday decorations, and seasonal business activities. The St. Michaels Business Association lists hours as Thursday and Friday 4 to 8 p.m., Saturday 10 a.m. to 8 p.m., and Sunday 10 a.m. to 2 p.m. St. Michaels Business Association

Easton Holiday Parade — Saturday, December 5, 2026
Discover Easton lists Easton’s Holiday Parade for Downtown Easton, MD, on December 5. This is a strong family-friendly community event and a useful Talbot County holiday listing. Discover Easton, Maryland

Christmas in St. Michaels — Thursday, December 10 through Sunday, December 13, 2026
Christmas in St. Michaels is set for St. Michaels, MD, from December 10 through 13. The official event site says the weekend benefits local nonprofit organizations and includes the town’s long-running holiday traditions. The event mailing address is listed as PO Box 873, St. Michaels, MD 21663, with contact email info@christmasinstmichaels.org. Christmas In St. Michaels

Oxford Holiday Market — Friday through Sunday, December 11 through 13, 2026
The Oxford Holiday Market returns to Oxford, MD, with more than two dozen artisan merchants, local foods, teas, family-friendly surprises, an Elf Hunt, and a visit from Santa on Saturday. The event page describes it as a small-town waterfront holiday market with local makers and seasonal gift shopping. Doehrn Tea Co.

Easton’s New Year Celebration / Crab Drop — Thursday, December 31, 2026, 9 p.m.
Discover Easton lists Easton’s New Year Celebration in the heart of Downtown Easton / Easton Town Center beginning at 9 p.m. This is the community New Year’s Eve event commonly known for the Crab Drop.