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Currently, in communities across the region, a great number of events and interpretive programs are in place.
These range from small local parades to large events such as the Waterfowl Festival in Easton. Some events are oriented toward local heritage, and others are celebrations of life on the Upper Eastern Shore.
Caroline County
- Caroline County Midwinter Performing Arts Series
Denton
- Caroline by Candlelight, House Tour
- Choptank River Yacht Club, Hydroplane Regatta
- Martinak Day
- Summerfest
- Choptank River Heritage Festival
Federalsburg
- Anything Goes Day
- Eastern Shore Threshermenās Show
- Marshyhope Bass Fishing Tournament
- Threshermanās Festival
Preston
Ridgely
- Strawberry Festival
- Jousting Tournaments
- Outlaw Days (Tuckahoe Partk)
Kent County
- Annual Christmas Shop and Exhibit
- Art in the Park
- Betterton Beach Day
- Christmas House Tour/Chestertown
- Country Crafts Guild Show
- Crumpton Candlelight Tour
- Halloween Parades
- Haunted Houses and Hayrides
- Kent County Fair and Horse Show
- Kent County Historical Trust Tour
- Marching Band Concert
- Maryland House and Garden Pilgrimage
- Music in the Park Series
- National Hunting and Fishing Day
- Rockfish Tournament
- Santaās Workshop
- Turnerās Creek Fishing Derby and Expo
- Washingtonās Birthday Ball
- Winterfest Weekend
Chestertown
- Antiques Show
- Candlelight Tour
- Chestertown River Regatta
- Chestertown Tea Party
- Crazy Days
- Festival of Trees
- Jazz Festival
- Wildlife Exhibition
Rock Hall
- Party on the Bay
- Rock Hall Sailing Regatta
Queen Anneās County
- Artists of the Chesapeake Annual Art Auction
- Christmas Boat Parade
- Eastern Shore Funfest
- Independence Day Celebration and Fireworks
- Annual American Cancer Society Crab Feast
- Olde Queen Anneās Day
- Thunder on the Narrows
- Wye of Carmichael Anniversary Homecoming
Centreville
- Annual Gala Auction
- Bay Country Music Festival
- May Day Celebration
- Queen Anneās County 4-H Fair
- Fall Artisan Festival
- Christmas Parade
- Holiday House Fair
- Fall Artisanās Festival
Church Hill
Grasonville
- Queen Anneās County Watermanās Festival
- Wetlands Fest
Kent Island
- Kent Island Days
- Kent Island Firemanās Carnival
- Spring Fling
- Watermanās Festival
Stevensville
- Annual Open Judged Art Show
- Kent Island Day
- Christ Church Bazaar
Sudlersville
Wye Mills
- Annual Queen Anneās County Eastern Shore Funfest
- Wye Parish Christmas Bazaar
Talbot County
- Annual Tuckahoe Steam and Gas Show
- Annual Memorial Hospital Classic Gold Tournament
- Delmarva Sportsman Show
- Eastern Shore Chamber Music Festival
- Eastern Shore Fall Festival Championship Jousting
- Tournament and Jack Russell Terrier Races
- Festival of Trees
- Mid-Atlantic Maritime Festival
- Springfest/Bounty of the Bay
- Talbot County Fair
- Talbot Kennel Clubās Annual Dog Show
Easton
- Annual Antiques Charity Show
- Arts Marketplace
- Dickens of a Christmas
- Eastern Shore Chamber Music Festival
- Festival of Trees
- First Night Talbot
- Harvest Hoe-down
- Octoberfest
- Old Tyme Fourth of July
- Talbot County Charity Antiques Show and Sale
- Waterfowl Festival
Oxford
- Oxford Days
- Oxford Fine Arts Festival
St. Michaels
- Christmas in St. Michaels
- Mid-Atlantic Maritime Arts Festival
- Concerts in the Park
- Strawberry Festival
- Antique and Classic Boat Festival
- Wooden Boat Show
- Independence Day Ceremony
- Crab Days
- Mid-Atlantic Small Craft Festival
- Fall into St. Michaels
- Pig and Crab Feast
- OysterFest
Trappe
Tilghman Island
- Tilghman Island Days Festival
- Tilghman Island Seafood Festival
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