Celebrating the Eastern Shore, Throughout the Seasons
Signature Eastern Shore events like Downrigging Weekend create new ways to enjoy each season.
Throughout the year, the communities of the Eastern Shore create different ways to celebrate the season. Distinctive to each county’s landscape and traditions, these festivals and events annually enliven life in Talbot, Queen Anne’s and Kent County. For locals, visitors and newcomers, they highlight the best of the Eastern Shore’s unique culture, music and cuisine. Community life here is strong, and these year-round events provide the chance to connect with your neighbors, enjoy music and local food, and savor the small town pace and energy the Eastern Shore never fails to offer.
Colonial costumes, reenactments, food, family fun, and a great parade are all part of Chestertown’s annual Tea Party Festival
SPRING
Talbot County: April 22: Oxford Day
This classic Chesapeake small-town festival kicks off spring with an old-school celebration of community, complete with a parade with homemade floats, a dog show, bake sales, marching bands and free rides on the Oxford Ferry.
Queen Anne’s County: April 14-16, Bay Bridge Boat Show
Held annually at Bay Bridge Marina, in Stevensville, MD, this spring powerboat show marks the beginning of boating season with lots of on-the-water eye candy. Whether you’re looking to upgrade your boat, take part in boating workshops and classes, buy new gear, or enjoy regional treats in a family friendly waterfront setting, this event is a great way to enjoy on-the-water living in Queen Anne’s County.
Kent County: May 25-28, Chestertown Tea Party Festival
This annual colonial-flavored street festival celebrates Chestertown’s 18th century history with a parade, colonial costumes, music, artisans, local food, and craft beer. The highlight of the day is the reenactment of the alleged 1774 Tea Party, with Chestertown’s costumed patriots dumping bales of tea into the Chester River. Other events throughout the weekend include a wine and beer festival on Sunday and a Raft Race.
Admire the animals and enjoy the rides at the annual Queen Anne’s County Fair, a local summer tradition.
SUMMER
Talbot County: August 13, Waterman’s Appreciation Day
The Chesapeake Bay Maritime Museum highlights the contributions and culture of Bay waterman at this summer festival that’s all things crabs, Chesapeake and community. Docking contests, boat rides, family activities, music and a community crabfeast mark one of the highlights of Talbot County’s glorious summer season.
https://cbmm.org/event/watermens-appreciation-day/
Queen Anne’s County: August 8-13, Queen Anne’s County Fair
This classic county fair celebrates the bounty of summer with livestock, crafts, and crops exhibits, carnival rides, a slate of different musical acts each evening, and crab cake dinners. Each evening features family-friendly entertainment, from a tractor pull to a dog show. Hosted by the Queen Anne’s County 4-H, the Fair is a traditional staple of Eastern Shore life, and a lot of fun for all ages.
Kent County: August 12-14, Pirates and Wenches Weekend
Rock Hall’s waterfront gets taken over by scurvy dogs, buccaneers, and pirates-at-heart in this fantasy weekend with a hometown spirit. Music, rum tasting, sea shanty singalongs, a dinghy parade, a treasure dig and more peg legs and parrots than you can count are all part of this fun in this family-friendly event.
The streets of Easton become a bird lover’s paradise during the annual Waterfowl Festival
FALL
Talbot County: November 10-12, Waterfowl Festival
Part wildlife art show and part sportsman’s expo, this town-wide festival celebrates all things Chesapeake, showcasing Easton’s historic downtown and centuries-old connection to waterfowl at the height of autumn’s full color. Meet the country’s finest wildlife painters, sculptors, carvers and photographers, and see their work in galleries spread across historic downtown Easton, while sampling crab soup and craft beer, enjoying dock dog contests, music, and more.
https://waterfowlfestival.org/
Queen Anne’s County: November 12, Bay Bridge Run
This epic, annual walk/ run 10k race provides the only chance to cross the Chesapeake Bay Bridge on foot. Participants take in glorious birds-eye views of sailboats, workboats and cargo ships from almost 200 feet above the Bay at the highest point. The course is point-to-point, covering the eastbound span of the bridge from Anne Arundel County to Kent Island in Queen Anne's County. The event finishes with a huge post-race party, complete with food trucks, craft beer and live music.
https://www.thebaybridgerun.com/
Kent County: October 27-29 Downrigging Festival
Chestertown’s Downrigging Weekend Festival, hosted by Sultana Education Foundation, is one of the largest annual tall ship gatherings in North America. Held on the Chester River and throughout the historic downtown, the festival features a long-weekend of tall ship sails, tours, live bluegrass music, lectures, exhibits, family activities, local oysters, fireworks, and more. Proceeds benefit the Foundation’s environmental literacy programs and the other nonprofits participating in the festival.
Decorated crab basket Christmas trees have become a more recent addition to the Eastern Shore’s holiday traditions.
WINTER
Queen Anne’s County: December 2, Waterman’s Crab Basket Tree Lighting
Hosted by the Queen Anne’s County Waterman’s Association, this event, launched during the pandemic, has grown over the last several years. The lighting of the Christmas trees, made up of individually decorated crab baskets, is the highlight of the day-long event which features an artisan village, the Blessing of the Fleet, visits from Santa, and carols from local Stevensville Middle School choir. The event is held at the Fisherman's Village Complex, near the Maryland Watermen’s Memorial on Kent Narrows.
https://www.kentnarrowsmd.com/holiday-basket-tree
Kent County: December 1 and 2, Dickens Festival
“Dickens of a Christmas” (or just Dickens to locals) celebrates the season with live music, carriage rides, Victorian food and drink, costumed characters, and entertainment all inspired by Dicken’s classic story, A Christmas Carol. The spirit of the season comes to life in several days of themed events, vendors, music and artisans throughout the historic downtown and shops.
https://mainstreetchestertown.org/events/dickens/
Talbot County: February 16 and 17, Chesapeake Fire and Ice Festival
In this unique cold-weather event, Downtown Easton’s historic district is ornamented with dozens of ice sculptures. The event kicks off with a Friday night Ice Block Party and features free live music and fire performances, live ice carving, outdoor ice skating, and the unveiling of the weekend’s ice sculptures with a free self-guided tour and light display.
