Queen Anne’s County

Centreville Farmers’ Market — Sundays in August and September, 9 a.m. to 1 p.m.
The Centreville Farmers’ Market is held on Centreville Main Street, 101 Lawyers Row, Centreville, MD 21617. The market is a good weekly public outing with local produce, handmade goods, and a walkable downtown setting. The Queen Anne’s County tourism listing describes it as every Sunday from 9 a.m. to 1 p.m. with local produce and handmade items.

First Saturdays Free Tours: Kennard African American Cultural Heritage Center — Saturday, September 5, 2026, 10 a.m. to 2 p.m.
The Kennard African American Cultural Heritage Center participates in Queen Anne’s County’s First Saturdays program, giving visitors a chance to learn more about local African American history and community heritage. The September 5 listing

Let Freedom Ring: A Revolutionary Birthday Bash — Saturday, September 26. Queen Anne’s County will mark America’s 250th anniversary with a community celebration from 10 a.m. to 2 p.m. on the Courthouse Green in Centreville. Plans include live music, food, historical demonstrations and exhibits, vendors and children’s activities, so this one should appeal to both families and history buffs.

Annual Faculty Show — Friday, October 16. The Queen Anne’s County Centre for the Arts will hold the opening of its Annual Faculty Show from 6 to 8 p.m. at the Centre for the Arts, 206 South Commerce Street, Centreville, MD 21617. The show is an opportunity to see work from the artists and instructors associated with the county arts program. For more information, contact the Centre for the Arts at 410-758-2520.

Centreville Day — Saturday, October 24. Downtown Centreville’s big fall community festival returns from 11 a.m. to 3 p.m., with a rain date of October 25. Activities take place along Lawyers Row, Broadway and the historic Courthouse Green in Centreville. Centreville Day is a free family festival with interactive activities and community organizations, and the event’s activities are advertised as free. For information, contact Centreville Main Street at 410-758-1180, ext. 17.

Caroline County

Caroline Summerfest — Friday, August 21 and Saturday, August 22, 2026
Caroline Summerfest returns to Downtown Denton, MD 21629, for a free two-day family festival. The event site lists the 2026 dates as August 21–22, and Downtown Denton describes it as the 37th annual Summerfest with live music, artisan booths, food, a Friday car show, Saturday fireworks, kids’ art activities, and more.

Talbot County

Outdoor Summer Concert: Motown and More — Friday, August 28, 2026, 7 p.m.
This concert is also listed for Harrison Street in front of the Tidewater Inn, Easton, MD 21601. The theme makes it especially audience-friendly for a classic-hits crowd, and the Easton calendar lists it as a 7 p.m. outdoor summer concert.

Free Summer Adventure Movie Series: National Treasure — Saturday, August 29, 2026, 2 p.m.
The Talbot County Free Library hosts this free movie event at 100 West Dover Street, Easton, MD 21601. Easton’s calendar lists free admission, refreshments, and presentation by the Talbot County Free Library and the Chesapeake Film Festival.

Outdoor Movie Night: Transformers One — Friday, September 4, 2026, 8:30 p.m. to 10:30 p.m.
Discover Easton lists this outdoor movie night at Idlewild Park, 115 Idlewild Avenue, Easton, MD 21601. The event is free and asks attendees to bring chairs and blankets for the movie under the stars.

CBMM Charity Boat Auction — Saturday, September 5, 2026
The Chesapeake Bay Maritime Museum lists its Charity Boat Auction for September 5 at CBMM, 213 North Talbot Street, St. Michaels, MD 21663. This is a strong public event for boat lovers, bargain hunters, and people who enjoy the St. Michaels waterfront.

Outdoor Movie Night: Coco — Friday, September 11, 2026, 8:30 p.m. to 10 p.m.
This outdoor movie night is scheduled for Moton Park, 51 Jowite Street, Easton, MD 21601. Discover Easton lists the film as being shown in Spanish with English subtitles, and it is part of the 2026 outdoor movie night series.

Mid-Shore Constitution Bowl — Saturday, September 12. The second annual Constitution Bowl will run from 9 a.m. to 1 p.m. at the Talbot County Free Library, 100 West Dover Street, Easton, MD 21601. The event focuses on knowledge of the U.S. Constitution and is part of the region’s America 250-related programming.

Talbot County Community Yard Sale — Saturday, September 19. Bargain hunters can browse a large community yard sale from 6:30 a.m. until noon at the Talbot County Community Center parking lot, 10028 Ocean Gateway, Easton, MD 21601. Admission for shoppers is free. Sellers pay for parking spaces and tables, and the rain date is September 26. For more information, call Talbot County Parks and Recreation at 410-770-8050.

Frederick Douglass Day — Saturday, September 26. Easton will celebrate the life and legacy of Talbot County native Frederick Douglass with its annual community observance centered around 11 North Washington Street in downtown Easton. The event is part of Discover Easton’s official 2026 calendar and offers an especially strong local-history connection for Mid-Shore residents.

Easton’s Fall Kickoff — Friday, October 2. Downtown Easton welcomes the fall season with its annual Fall Kickoff on October 2. The community event is centered in downtown Easton and is part of Discover Easton’s official 2026 event schedule, with seasonal activities designed to encourage people to explore downtown shops, restaurants and attractions.

Halloween BOOnanza — Wednesday, October 28. Talbot County Parks and Recreation will turn the Talbot County Community Center, 10028 Ocean Gateway, Easton, MD 21601, into a family Halloween destination from 6 to 8 p.m. Activities include ice skating, trick-or-treating, face painting, photo opportunities and costumes. Admission is $10 per child, with children age two and under free, and no advance registration is required. For information, call 410-770-8050.

KENT COUNTY

Paper Trails 2: Stories & Storage Tips from the Library Project — Thursday, September 10. The Historical Society of Kent County will host a free public talk and mini-workshop from noon to 1 p.m. at the Bordley History Center, 301 High Street, Chestertown, MD 21620. Museum professional Lana Faber will talk about the society’s Library Inventory Project and give practical advice on caring for and storing paper artifacts at home.

Chestertown Jazz Festival — Saturday, September 12. The Chestertown Jazz Festival celebrates its 30th anniversary with music from noon to 6 p.m. at Wilmer Park in Chestertown. Five bands are scheduled under the large festival tent overlooking the Chester River. Tickets are listed in the $40–$50 range.

Chestertown Challenge Half Marathon and 5K — Sunday, October 11. Runners and walkers will gather at Wilmer Park in Chestertown, with registration beginning at 8 a.m. and the Half Marathon, 5K Run and 5K Walk starting at 9 a.m. The event benefits the Kent Association of Riding Therapy. For GPS purposes, organizers recommend using 400 South Cross Street, Chestertown, MD 21620, which is directly across from Wilmer Park.

Chestertown Halloween Parade — Saturday, October 31. The Chestertown Lions Club’s annual parade steps off at 1 p.m. along High Street in downtown Chestertown and runs until about 3 p.m. Expect floats, marching groups, costumed characters, pets and plenty of Halloween decorations.