Queen Anne’s County Fair, Livestock Shows, 4-H, Entertainment, Fun for

Dirty Rotten Scoundrels
August 13-23, 2026

Sophisticated, hilarious, and packed with

The Ricky Wise Trio performs a free outdoor concert in the 2026 Summer Free Concert Series at Mark Cascia Vineyards in Stevensville on Kent Island. The performance runs from 7

A great assortment of food vendors ie fruit/veggies/meat/eggs/honey/sourdough breads and pastries/mushrooms/ microgreens/juices/olives,EVOO,balsamic/lots

Musical Comedy

Two con men, a beautiful woman and the elite of the French Riviera collide in a “sexy and irreverent farce.” After meeting on a train, two swindlers

Concerts are BYOC (Bring Your Own Chairs) OR blankets! Make sure to also bring your family, friends, neighbors, and/or four-legged pals (leashed, of course ).
We’ll

Chestertown’s beloved Legacy Day returns in August 2026, celebrating African American history, culture, and community through music, storytelling, food, and fellowship.

Enjoy a two-hour sail aboard the Skipjack Nathan! We tell stories, learn about the history of Skipjacks, enjoy scenic views, and dredge for oysters. Each sail is unique

We’re excited to host our second annual Members Exhibition!
Current members, valid through August 1, 2026, may submit one artwork in any 2D or 3D medium. Maximum size

One of the largest annual music and cultural festivals in Cambridge, MD. The street festival is free, food trucks, vendors, and Community Stage. The Main Stage concert at

Experience an unforgettable evening of music with the Commercial Music Group! Join us for a show of captivating performances that you won’t want to

Immerse yourself in history by stepping back to agrarian life and viewing an assortment of historic farm equipment. Walk the nature trails, explore the 1628-1840 Stavely family

Join us for our annual Blue Moon Tent Sale August 15th & 16th from 9am-4pm. Everything in the store and under the tents will be 50% off. Furniture, accessories, gifts, art,

Located in the heart of Centreville, the Centreville Farmers’ Market is not your average market; it’s quickly becoming a hustling hub of artisanal craftsmanship and local

Concerts are BYOC (Bring Your Own Chairs) OR blankets! Make sure to also bring your family, friends, neighbors, and/or four-legged pals (leashed, of course ).
We’ll

Honey Sol performs a free outdoor concert in the 2026 Summer Free Concert Series at Mark Cascia Vineyards in Stevensville on Kent Island. The performance runs from 7 to 9 p.m.,

Come on out to Cars On High in Chestertown, MD to show off your pride and joy. This event is held on the 3rd Thursday, from 6-8PM, April thru

A great assortment of food vendors ie fruit/veggies/meat/eggs/honey/sourdough breads and pastries/mushrooms/ microgreens/juices/olives,EVOO,balsamic/lots

Caroline Summerfest is a free, family entertainment festival featuring two stages of regional & local entertainment, Saturday fireworks show, strolling performers,

Free

Eastern Shore Jousting Association’s

Music on the Marshyhope is a free seasonal outdoor concert series held at the Federalsburg Marina (Marina Park) in Federalsburg,

Located in the heart of Centreville, the Centreville Farmers’ Market is not your average market; it’s quickly becoming a hustling hub of artisanal craftsmanship and local

Intro to Horn Point Lab; physical oceanography; coastal resilience; oyster

Open Mic Night is back with Ford Schumann at the Garfield Center For the Arts at the Prince Theatre!

Play music on your own or with a band, read some poetry, do a

Concerts are BYOC (Bring Your Own Chairs) OR blankets! Make sure to also bring your family, friends, neighbors, and/or four-legged pals (leashed, of course ).
We’ll

A great assortment of food vendors ie fruit/veggies/meat/eggs/honey/sourdough breads and pastries/mushrooms/ microgreens/juices/olives,EVOO,balsamic/lots

The Cambridge Main Street Farmer’s Market is open each Thursday, from mid-April through mid-November,

Learn the eerie true stories along High Street in Cambridge – said to be the most haunted street in

The Mainstay is pleased to welcome the acclaimed international duo Ariella and Nicolaas for their debut performance on Friday, August 28th. Blending soulful vocals, fiery

Held in the Chester River, our tournament promotes the removal of non-native and invasive species while raising money for Maryland Wildlife & Heritage Association, an

Artist

Free

Get ready for an exciting day packed with cool cars, great music, family fun, and community spirit—all while supporting the Greensboro Community Basketball

Located in the heart of Centreville, the Centreville Farmers’ Market is not your average market; it’s quickly becoming a hustling hub of artisanal craftsmanship and local

The Taylors Island Boat Docking Challenge features the best captains on the Chesapeake hustling to see who can dock a workboat the fastest. It benefits the Taylors Island

Get your custom cars, classic cars, hot rods and motorcycles ready to roll down the mile-long lane on Benedictine’s campus in Ridgely, Maryland!

Join us for a celebratory event commemorating America’s 250th anniversary in 2026 with live music, vendors, representation from various historic sites, food, drinks,

Every day, Baywater Animal Rescue gives vulnerable animals a second chance. Whether it’s providing emergency medical care to an injured stray, rescuing