Queen Anne’s County

Centreville Farmers’ Market — 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.

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.

Talbot County

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.

Every step has a story. Every story deserves to be heard. – This October 21, the Mid-Shore Council on Family Violence invites the community to experience SOLE Strength, an immersive art exhibition transforming the stories and journeys of domestic violence survivors into powerful works of art. Through shoes, survivor stories, sound and visual art, visitors are invited to listen, reflect and walk alongside survivors as they move toward safety, healing and self-sufficiency.  The Gallery Reception takes place on Wednesday, October 21 with two showings at 5pm and 7pm at Market at Dover Station in Easton, featuring the unveiling of 28 custom works of art created by an extraordinary group of regional artists. The $75 ticket includes delicious food prepared by Chef Jordan Lloyd of Hambleton House, appetizers, a dessert station hosted by Emily’s Produce of Cambridge, a signature drink, and an opportunity to experience the exhibition and bid on the artwork in support of survivors. The first 100 people to sign up will receive SOLE Strength wireless earbuds, allowing them to listen to the accompanying survivor audio stories throughout the exhibition.  Learn more at mscfv.org.

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

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.

Dance with the Stars A Night in the Enchanted Forest – Celebrate community and support Horizons of Kent and Queen Anne’s in a dazzling night of music and dance.  November 14, 2026.  You can also vote for your favorite dancers.  Tickets/Tables/Votes are on sale NOW!  Please visit:https://

horizonskentqueenannes.org/dance-with-the-stars-2026-1

 Questions? Email us at events@horizonsKQA.org

Caroline County

Denton Cruise-In Car Show — Friday, October 9. The final scheduled downtown Cruise-In of the season runs from 6 to 8 p.m. on the 200 block of Market Street, Denton, MD 21629. Classic cars, trucks and motorcycles line the street while visitors enjoy music and a walk through downtown. Vehicle owners interested in participating can contact the Denton Police Department at 410-479-1414.

Pumpkin Palooza and Halloween Parade — Friday, October 30. Downtown Denton celebrates Halloween beginning at 5 p.m. with Pumpkin Palooza and the town Halloween parade. The activities are centered around Market Street in downtown Denton, MD 21629, with vendors, community groups, costumed participants and parade entries.

Native Seed Cleaning Workshop — Thursday, November 5. A free public workshop will be held from 6 to 7:30 p.m. at the Caroline County Public Library, 100 Market Street, Denton, MD 21629. Environmental Concern and Wild Ones Delmarva will demonstrate how to collect and clean native plant seeds, with hands-on activities and information for gardeners interested in supporting birds, insects and other local wildlife.

Annual Denton Holiday Parade and Lighting of the Green — Thursday, December 3. Downtown Denton will celebrate the Christmas season beginning at 6 p.m. with the annual parade and Lighting of the Green. Activities take place around Market Street and the downtown Denton business district. Several downtown streets will be closed during the celebration. For information about town events, contact Denton Main Street at 410-924-2328 or Caroline County Recreation and Parks at 410-479-8120.