Queen Anne’s County

County Wide Scavenger Hunt — Through August 31, 2026
This summer-long Queen Anne’s County activity runs through the end of August and is built around the Goosechase app. Visitors and locals can play for a day or throughout the season, completing local challenges for points and a chance at prizes. The tourism listing describes it as a countywide “Support Local” scavenger hunt, so there is no single event address. For general visitor information, contact Queen Anne’s County Tourism at 410-604-2100, 425 Piney Narrows Road, Chester, MD 21619.

Sudlersville Peach Festival — Friday, July 31, 2026, 6 p.m. until fireworks, and Saturday, August 1, 2026, 10 a.m. to 3 p.m.
The Sudlersville Peach Festival is held at Godfrey’s Farm, 302 Leager Road, Sudlersville, MD 21668. This is a free, family-friendly festival with live music, local food, peach treats, vendors, and community activities. The Queen Anne’s County listing confirms the Saturday hours and notes the Friday evening portion with fireworks.

First Saturdays Free Tours: The Hope School — Saturday, August 1, 2026, 10 a.m. to 2 p.m.
This First Saturday event gives the public a chance to visit one of Queen Anne’s County’s historic sites. The event follows the county’s First Saturdays format, with free public tours from 10 a.m. to 2 p.m. The tourism listing places it alongside the August 1 First Saturday schedule. For general historic-site information, use Queen Anne’s County Tourism at 410-604-2100.

Queen Anne’s County 4-H Fair — Monday, August 10 through Saturday, August 15, 2026
The Queen Anne’s County 4-H Fair is held at the Queen Anne’s County 4-H Park, 100 Dulin Clark Road, Centreville, MD 21617. This is the county’s major agricultural fair, with 4-H exhibits, livestock, food, family activities, and the kind of classic county-fair atmosphere that works well for families and longtime Shore residents. The fair site lists the 2026 fair dates as August 10–15.

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 shows the event running from 10 a.m. to 2 p.m.

Kent County

Chestertown Farmers’ & Artisans’ Market — Saturdays in August and September, 8 a.m. to noon
The Chestertown Farmers’ & Artisans’ Market takes place around Fountain Park / Park Row, Chestertown, MD 21620. It is one of Kent County’s easiest ongoing public events to recommend, with local produce, baked goods, flowers, meats, cheeses, and artisan items in the middle of downtown Chestertown. A market contact number listed by Maryland’s Best is 443-480-1893.

Chestertown Recycling Booth — Saturdays in August and September, 9 a.m. to noon
The Chestertown Environmental Committee operates a recycling booth at the Chestertown Farmers’ & Artisans’ Market, Park Row / Fountain Park, Chestertown, MD 21620. This is a practical community stop for residents who want to recycle hard-to-recycle items such as batteries, bottle caps, toothpaste tubes, toothbrushes, corks, makeup containers, and filters. Main Street Chestertown lists the booth as running Saturdays from 9 a.m. to noon at the farmers’ market.

Chestertown First Friday — Friday, August 7, 2026, 5 p.m. to 8 p.m.
Downtown Chestertown’s First Friday gives people a reason to stroll the shops, galleries, and restaurants in the historic business district. Main Street Chestertown lists the August First Friday for 5 to 8 p.m., with downtown shops staying open later and galleries hosting openings and special events. The event is centered in Downtown Chestertown, MD 21620.

Common Tables Exhibition — August 7 through August 29, 2026, 11 a.m. to 3 p.m.
Main Street Chestertown lists the Common Tables Exhibition beginning August 7 and continuing through August 29, with hours shown as 11 a.m. to 3 p.m. This is an arts-and-community style listing rather than a bar or theatre event. The listing appears on the Main Street Chestertown August 2026 events calendar.

Chestertown First Friday — Friday, September 4, 2026, 5 p.m. to 8 p.m.
September First Friday brings another evening of downtown shopping, gallery activity, and community strolling in Downtown Chestertown, MD 21620. Main Street Chestertown describes First Friday as a free monthly event sponsored by downtown merchants, community organizations, and galleries. Their office contact is 410-778-2991, located at 122 North Cross Street, Chestertown, MD 21620.

Chestertown Jazz Festival / Jazz by the River — September 2026 listing, Wilmer Park
The Chestertown Jazz Festival is a major annual music event tied to Wilmer Park, 413 South Cross Street, Chestertown, MD 21620. The available Main Street page I found was still carrying the prior-year festival detail, but it identifies the event as Jazz by the River in Wilmer Park and lists Main Street Chestertown contact information at 410-778-2991. I would verify the exact 2026 date directly before publishing this one as a hard calendar item.

Caroline County

Caroline-Dorchester County Fair — Wednesday, August 5 through Saturday, August 8, 2026
The Caroline-Dorchester County Fair is scheduled for August 5–8, 2026, at the Caroline County Fairgrounds / Caroline County 4-H Club and Youth Park, 8230 Detour Road, Denton, MD 21629. This is a major family-friendly county fair with 4-H, livestock, indoor exhibits, contests, food, and community activities. The fair site lists 302-566-8076 and 4h.fairboard@gmail.com as contact information.

Denton Friday Night Cruise-In Car Show — Friday, August 14, 2026, 6 p.m. to 8 p.m.
The Denton Friday Night Cruise-In Car Show runs through October in historic Downtown Denton, around the 200 block of Market Street, Denton, MD 21629. It is a free family event with cars, motorcycles, food, and a DJ. Caroline County Tourism lists the series as second Fridays, 6 to 8 p.m.

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

First Friday Gallery Walk — Friday, August 7, 2026
Discover Easton lists a First Friday Gallery Walk on North Harrison Street, Easton, MD 21601, for August 7. This is a public downtown arts-and-shopping event rather than a theatre or bar event, and it fits well for a community calendar audience looking for something casual in Easton.

Outdoor Movie Night: The Rocketeer — Friday, August 7, 2026
This free outdoor movie night is scheduled at Easton Airport, 29051 Corkran Road, Easton, MD 21601. Discover Easton lists the movie as part of the 2026 outdoor movie schedule and notes that guests should bring chairs and blankets.

Outdoor Summer Concert: U.S. Air Force Singing Sergeants — Saturday, August 8, 2026, 7 p.m.
Easton’s community calendar lists this outdoor concert for Harrison Street in front of the Tidewater Inn, Easton, MD 21601, with a 7 p.m. start. It is a public summer concert in downtown Easton and is not listed as a theatre or bar event.

Free Summer Adventure Movie Series: Stand By Me — Saturday, August 8, 2026, 2 p.m.
This free public movie program is scheduled at the Talbot County Free Library, 100 West Dover Street, Easton, MD 21601. The Easton calendar lists free admission and refreshments, with presentation by the Talbot County Free Library and the Chesapeake Film Festival.

Watermen’s Appreciation Day — Sunday, August 9, 2026, 10 a.m. to 4 p.m.
The Chesapeake Bay Maritime Museum holds Watermen’s Appreciation Day at CBMM, 213 North Talbot Street, St. Michaels, MD 21663. The museum describes it as its annual celebration of the men and women who make their living on the Chesapeake Bay and their heritage.

Outdoor Summer Concert: U.S. Army Field Band — Saturday, August 15, 2026, 7 p.m.
This outdoor concert is listed for Harrison Street in front of the Tidewater Inn, Easton, MD 21601. It is another free-style downtown summer concert option that should work well for a general public events listing.

Outdoor Summer Concert: U.S. Navy Band Cruisers — Saturday, August 22, 2026, 7 p.m.
The Easton calendar lists the U.S. Navy Band Cruisers on Harrison Street in front of the Tidewater Inn, Easton, MD 21601. This gives Talbot County another public outdoor music option during late August, separate from theatre listings.

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.