Chestertown Taste of the Town

Chestertown Taste of the Town

May 1, 2016

The 10th Annual Taste of the Town (& County) will be Sunday, May 1, 2016. Noon to 3pm. Spend an afternoon sampling signature dishes from Chestertown & Kent County's finest restaurants and caterers. Featured dishes range from nouvelle gourmet to regional classics such as Maryland Crab Soup. Diners will want to come early to view the Paint the Town artwork exhibited in Fountain Park.

Galena Dogwood Festival

Galena Dogwood Festival

May 7, 2016

The annual Galena Dogwood Festival is set for Saturday. May 7, 2016. It will take place throughout Galena from 9am–5pm. Parade at 10am. There will be a Baby Contest, Crafts, Demonstrations, Exhibits and an Amusement Park. Family Oriented Magic, Mime, Story Telling, Song and Dance, Juggling and Monkey Business, 5k and plenty of Eastern Shore Food.

Chestertown Tea Party

Chestertown Tea Party

May 27 - 29, 2016.

Start the weekend Friday night at the Block Party to kick-off the celebration of the Tea Party Festival, the Block Party is sure to be a hoppin’ good time! Come for the food, live music, other entertainment. There will be fun for all ages! Then on Saturday come downtown to commemorate the local merchants' revolt against the British tea tax. Starting with the 5k and 10 mile Distance Run, then a reenactment, parade, concessions, & crafts. On Sunday come out to the Beer, Wine Tasting and Raft Race at noon and enjoy a crazy race of home made rafts while sampling craft beer and local wine. The day would not be complete without music, food and craft vendors.

Chestertown Tea Party Website

National Music Festival

National Music Festival

June 5 - 18, 2016

The Festival's 6th season, in Chestertown, Maryland, brings together world-class mentors and gifted apprentice musicians on the cusp of their professional careers. The two groups rehearse and perform together at Washington College and throughout the Eastern Shore in orchestral, chamber, solo recital, vocal, choral and chamber opera repertoire.

Music in the Park

Chestertown's "Music in the Park" Summer Concert Series

Every other Saturday, beginning June 11, 2016

Free outdoor concerts! Every other Saturday evening beginning June 11, 2016, from 7-8:30 pm Chestertown’s “Music in the Park” concert series presents the best in local & regional music – including big band, bluegrass, folk, jazz, rock, and more! Bring a chair and join us. Saturdays - June 11, 15, July 2, 16, 30, Aug 13, 27. Rain location Emmanuel Episcopal Church across from park. Sponsored by Town of Chestertown, Kent County Arts Council, and community contributors like you. Please send donations marked for “Music in the Park” to Town of Chestertown, 118 N Cross St, Chestertown, MD 21620

Fourth of July in Kent County

Fourth of July in Kent County

Many events are planned to make your July 4th holiday celebration a memorable one.

Kent County 4H Fair

Kent County 4H Fair

July 21 - 23, 2016

4-H Exhibits, live stock auction, music, great food and lots more. Kent AG Center, Tolchester.

Kent County Fair Website


Betterton Appreciation Day

Betterton Day

Saturday, August 6, 2016

Join us for a fun-filled day at Betterton Beach! Parade starts down Main St. at 10:30am followed by rides, crafts, food and vendors at the beach. Free Admission. Parking and Rides Avaliable.

Pirates and Wenches Fantasy Weekend

Pirates and Wenches Fantasy Weekend

Friday - Sunday, August 12 - 14, 2016

Avast me hearties! Buccaneers and landlubbers of all ages -- come by land or come by sea for a town-wide waterfront theme party that you won't forget! Sea shanty sing-a-long, decorated dinghy flotilla and race, beach party, pirate's ball, treasure hunts, costume contests, live entertainment, merchants, mayhem on Main Street and much more for the whole family! Costumes and acts of piracy encouraged!

Pirates and Wenches Fantasy Weekend Website

Harry Potter Festival

Harry Potter Festival

September 30 - October 1, 2016

Grab your wand, hop on a broom and come for a weekend of magic, on Friday and Saturday October 2nd and 3rd, 2015 at Chestertown Harry Potter Festival. The colonial river town will host the celebration, featuring spectacular activities and events for children and adults – wizards and muggles alike. Proudly, presented by the non-profit Mid-Shore Community Foundation, the Festival benefits the Garfield Center for the Arts, a cultural organization that nurtures, celebrates and supports arts and artists through performance and education

Chestertown RiverFest


Saturday, September 24  12:00 p.m. - Sunset.
Wilmer Park and foot of High Street
Chestertown RiverArts and Washington College Center for Environment & Society are launching a new event, Chestertown Riverfest, on September 26, 2015 at Wilmer Park and the foot of High Street. The event is open to the whole community and will feature the unveiling of a large, floating, solar-powered sculpture on the river, the 9th annual cardboard boat regatta, kayak and canoe races, a poker run, as well as live music, food, and kids activities. There will be something for everyone at this event, so bring the whole family! For more information or to register fro paddling events, call RiverArts Chestertown at (410) 778-6300 or visit



Historic tour of Chestertown Maryland

Chestertown Historic Walking Tour

Saturday, October 1, 2016
Celebrating our 45th Annual Historic Hour Tour, this year we focus on your favorite 18th century residences as well as inspirational uses of ‘newer’ historic properties. Some of this year’s homes feature period furnishings and grand vistas of the Chester River; others, fantastic designs for today’s living in historic spaces. The houses are open Saturday, October 3rd from 1pm to 5pm. Tickets are $25 in advance, and also available the day of for $35. All tickets are available beginning at 11am at the Bordley History Center, located across from Fountain Park at 301 High Street. To reserve your ticket in advance, or for more information, please call the Kent County Historical Society at (410) 778-3499 or visit
Rock Hall's Fall Fest

Rock Hall Fall Fest

Saturday, October 8  10:00 a.m. - 4:00 p.m.
Rock Hall's annual homage to the mighty oyster and thank you to the town. Music all day, craft vendors lining the street, and a FREE Kids Kourt. Join us! For more information, please visit
Sultana Downrigging

Sultana Downrigging

Friday, October 28 - Sunday, October 30, 2016
Now in its fifteenth year, Sultana’s Downrigging Weekend Tall Ship and Wooden Boat Festival has evolved into one of the largest annual Tall Ship gatherings on the East Coast. Visitors to festival can expect to see a waterfront packed with ships, schooners, and wooden boats; performances by world-class musicians; lectures by nationally recognized authors and filmmakers; plenty of opportunities to go sailing as part of a fleet of “Tall Ships”; and the chance to spend the weekend in Chestertown – one of America’s best preserved historic seaports. Don’t miss it! For more information, please visit


Annual Chestertown RiverArts Studio Tour

Chestertown RiverArts Studio Tour

Saturday, October 22 and Sunday, October 23
Saturday, October 29 and Sunday, October 30
Here's the chance to enter into the working studios of area artists and craftspeople, ask questions, see them at work and get a chance to purchase incredible art at studio prices. The self guided Studio Tour will include studios in Chestertown, Rock Hall, Galena, Betterton, and Church Hill.  For more information, please visit


Holiday events in Kent County, MD

Join us for the Holidays

The spirit of the holidays can be found all over Kent County. Craft shows and fairs, holiday concerts, parades and house tours are just a few of the many events happening this holiday season in Kent County. Join us in celebrating this festive season.

Rock Hall New Years Eve

New Years Eve in Rock Hall

Rock Hall Crawl Chasin' th' Blues to 2015. Bring in the new year...Eastern Shore (Mardi Gras) style. Parade of crazy hats at 6:00 p.m. on Main Street. Annual Hat Competition-Prizes awarded on Main St. at 7:30 p.m. Street Music throughout the night at several venues. Count down the new year, with the famous “Rockfish Drop” at midnight at the Rock Hall Harbor Bulkhead. For more information, please call Rock Hall Town Office at 410-639-7611.