Come celebrate at our family based Carnival on High! Our second annual family carnival will be Saturday July 1st from 5-8pm at the foot of High Street! Join us for delicious carnival food, face painting, carnival games, train rides, and much much more! This year we are including the famous Bubble Dad to entertain children […]
Put on by RiverArts, this plein air event has artists paint the local scene and make their paintings available for sale. There is a two-hour Quick Draw; these paintings are then shown in Fountain Park, are judged, and also for sale.
Reserve Your Seat at the Table for Dining Under the Stars Dinner Series at Brampton Inn! Guest Chef Kurt Peter from Chesapeake Chef Service will craft an indulgent multi-course feast that spotlights the “cream” of the Chesapeake’s crop, including farmers, ranchers, artisanal producers, micro-brewers, distillers and winemakers. Born and raised on the Eastern Shore, Chef […]
The Brampton Gourmet Club is one HOT ticket! Starring Easton-based Guest Chef Jordan Lloyd, from Hambleton House, with historic Brampton Inn, in Chestertown, Maryland, providing a visually spectacular backdrop - prepare to embark on a cinematic and gastronomic journey like never before! Here’s where Lloyd, an award-winning chef and TV personality takes cinephiles, foodies and […]
The Chestertown Tea Party festival is a time honored tradition for visitors and residents alike. This weekend long festival has entertainment for all ages. Kick off the Tea Party weekend with the Friday Night Block Party, hosted by Main Street Chestertown. The Block party includes music, food trucks and vendors, beverages, and fun for all […]
The National Music Festival transforms Kent County into a hub of music. The nationally recognized event will feature music to suit virtually every taste — from symphonies and chamber music to hints of jazz. More than 30 concerts and over 200 open rehearsals are scheduled throughout the festival in venues across the Eastern Shore.
Friday, June 14th, 2024, and Saturday, June 15th, 2024, the Bayside H.O.Y.A.S., will host their annual “Heroes of the Chesapeake” Juneteenth celebration at Fountain Park in Chestertown, Md. This two-day celebration will include live musical performances by Best Kept Soul and Sombarkin’. The two-day celebration will also include a living history performance by nationally recognized […]
Join us for an Open House at Brampton 1860! Explore the historic charm of Brampton 1860 a boutique hotel and venue located at 25227 Chestertown Rd. This in-person event offers a unique opportunity to step back in time and experience the beauty of this iconic location. Discover the rich history behind Brampton 1860. Learn about […]
Hosted by the Downtown Chestertown Association, Crazy Days is Chestertown’s annual sidewalk sale with businesses offering crazy deals and restaurants offering crazy specials.
The Sultana Education Foundation's Downrigging Weekend highlights Tall Ships and Bluegrass, along with nautical history and Chesapeake Bay ecology.
