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Upcoming June Events in Kent County

June 1 @ 8:00 am - June 30 @ 5:00 pm

A Cabaret: The Uptown Club

June 1 | 7:30-9:30 p.m.

Sumner Hall, 206 South Queen Street, Chestertown

Come to the Cabaret and enjoy music of the 1950s, 60s and 70s. This event is co-sponsored by Sumner Hall and RiverArts as part of its celebration of African American tradition-bearers. Sumner Hall is one of two existing African American G.A.R. buildings still standing in the United States and the only one offering regular programs. Built circa 1908 and fully restored in 2014, it serves today as a museum, education site, performance stage, social hall, gallery and community center. For details, call 443-282-0023 or 410-778-6300 or email info@garpost25.org or visit garpost25.org.

Golf Tournament Fundraiser

June 1 | 10 a.m. Check In; Noon Tee Time

Chester River Yacht and Country Club, Chestertown

Raising $200,000 to replace laparoscopic/arthroscopic surgical equipment that are used by nine surgeons for exploration, diagnosis and treatment at University of Maryland Shore Medical Center at Chestertown. To register, call 410-810-5660 or email mruehrmund@umm.edu.

History Happy Hour

June 1 | 4 p.m.

Historical Society of Kent County, 301 High Street, Chestertown

Listen to an informative history lecture while enjoying a glass of wine. For details, call 410-778-3499 or email admin@kentcountyhistory.org.

First Friday

June 1 | 5-8 p.m.

Chestertown Historic District

Flock to downtown for this monthly progressive open house. Businesses keep their doors open later so everyone can enjoy gallery exhibits, unique shopping, special performances, kids’ activities and a variety of dining options. This is one of Chestertown’s most beloved social events. For more information, contact the Downtown Chestertown Association at downtownchestertown@gmail.com.

Juried Painting and Contemporary Craft Exhibit

June 1 | 5-8 p.m.

Chestertown RiverArts, 315 High Street, Suite 106

The Juried Painting and Contemporary Craft Exhibit will be on display in both galleries through June 30. There will be an opening reception on First Friday, June 1 from 5 to 8 p.m. Gallery hours: Tuesday-Friday (11 a.m.-4 p.m.), Saturday (10 a.m.-4 p.m.), and Sunday (11 a.m.-3 p.m.).

Sultana Public Paddles

June 2 (Saltmarsh Paddle)

June 7 (Mount Harmon Tour)

June 9 (Oysters and Indians)

June 16 (Osprey Paddle)

Sultana Education Foundation, 200 South Cross Street, Chestertown

Join Sultana Education Foundation’s staff naturalists for a unique kayak paddles on Maryland’s Upper Eastern Shore. Kayaks for these trips are provided. Bring water, a snack, and binoculars. Paddles take place from 10 a.m. to 12:30 p.m. For reservations, call 410-778-6954 or email lbrocker@sultanaeducation.org.

Sultana Public Sails

June 2 | 11 a.m.-1 p.m. and 2-4 p.m.

Sultana Education Foundation, 200 South Cross Street, Chestertown

Departing and returning from Sultana’s home port of historic Chestertown, Sultana’s two-hour public sails are a great way to sail the Chester River onboard a traditional schooner. Passengers are encouraged to help raise the sails, steer using Sultana’s seven-foot long tiller, and explore the authentically reproduced crew’s quarters below-decks. For details, contact 410-778-6954 or lbrocker@sultanaeducation.org.

Uptown Vocal Jazz Quartet Concert

June 2 | 8 p.m.

The Mainstay, 5753 Main Street, Rock Hall

Heralded as “electrifying” and “pure fun,” Uptown Vocal Jazz Quartet built a loyal audience across five continents with their stylized arrangements of head-turning original songs and harmonically rich renditions of American Songbook classics. With their tight harmonies, engaging presentation and vocal sass, Uptown Vocal Jazz Quartet has put their creative signature on the group vocal style that mixes great fun with great art. They have been highly celebrated for extending the vocal jazz repertoire beyond standards and made their own songbook of originals the spotlight of their ear-popping arrangements. Call 410-639-9133, email info@mainstayrockhall.org or visit mainstayrockhall.org for tickets.

National Music Festival

June 3-16

Various times and locations throughout Kent County

The National Music Festival is a world-class celebration of music, bringing together professional mentors and gifted apprentice musicians on the cusp of their professional careers. The two groups rehearse and perform together throughout Kent County in orchestral and chamber repertoire. All rehearsals are free and open to the public. Some concerts are free; others require a ticket. From a solo violinist to a massive symphony orchestra with chorus, from Beethoven to symphonic jazz, find it all at the National Music Festival. For details, visit www.nationalmusic.us or call 443-480-0221.

String Quartet Preview Performance

June 5 | 12:30-1:15 p.m.

Sumner Hall, 206 South Queen Street, Chestertown

A special musical experience in an intimate setting by one of the groups that will later play at one of the larger National Music Festival venues. No admission fee.

Antique Airplane Fly-In

June 9 | 10 a.m. to 2 p.m.

Massey Aerodrome, 33541 Maryland Line Road, Massey

The 47th Antique Airplane Fly-In at Massey Aerodrome will be conducted by the Potomac Antique Aero Squadron. Good weather will attract over 100 antique and classic aircraft, many taildraggers and biplanes. Watch them land and take off from the excellent photo and viewing area overlooking the runway. Hear the unique sound of radial engines. Tour the Massey Air Museum, DC-3 and hangars. Free Admission. The Millington Fire Company will be selling refreshments. For details, contact 410-928-5270, email@masseyaero.org or visit http://masseyaero.org.

One-Design Regatta

June 16-17 | 8 a.m.-5 p.m.

Rock Hall Yacht Club, McKinleyville Road, Rock Hall

The Rock Hall Yacht Club hosts the Annual Summer One-Design Regatta inviting all one design sailboat classes to compete in a two-day sailboat regatta in Langford Bay and the Chester River. Call 410-639-2182 or visit RockHallYachtClub.org.

Juneteenth Celebration

June 16 | 7-10 p.m.

Sumner Hall, 206 South Queen Street, Chestertown

Also called Freedom Day or Emancipation Day, Juneteenth celebrates the abolition of slavery in the United States. This year enjoy an evening of jazz, featuring 3 J BLUE, to celebrate African American freedom, heritage and culture. Ticket price of $15 includes snacks and soft drinks. Alcoholic beverages will be available for an additional donation to Sumner Hall.

Cars on High

June 21 | 6-8 p.m.

300 block of High Street – Downtown Chestertown by Fountain Park

Classic, exotic, antique and customized cars are on display in the 300 block of High Street. Come admire the rides and chat with the proud owners. This season opener features music by the popular High and Wides band. Food trucks will be on site, too. For details, call 410-778-2991 or email CarsOnHighChestertown@gmail.com. Sponsored by Main Street Chestertown, Cars on High will continue on the third Thursday of the month, weather permitting, through October.

Short Attention Span

June 22-23, 29-30 | 8 p.m.

June 24, July 1 | 3 p.m.

Garfield Center for the Arts, 210 High Street, Chestertown

Short Attention Span Theatre is an annual 10-minute play festival. For tickets, call 410-810-2060 or email boxoffice@garfieldcenter.org.

Grand Ole Ditch Concert

June 23 | 8 p.m.

The Mainstay, 5753 Main Street, Rock Hall

Grand Ole Ditch is all about having some new fun with that old Appalachian sound. The band brings high-energy and a youthful perspective to the bluegrass genre. Covering genres from old-time to bluegrass and even a little Stevie Wonder, this band is sure to thrill traditionalists and new listeners. For tickets, call 410-639-9133 or email info@mainstayrockhall.org.

Bay To Bay Bicycle Ride

June 24 | 6:30 a.m.-4 p.m.

Betterton Fire Hall, Betterton

The Chestertown Lions Club will host the 33rd Annual Bay to Bay Bicycle Ride. Start at Betterton Fire Hall on the Chesapeake Bay and ride to the Delaware Bay and back. The Bay to Bay ride is 102 miles. Routes from 26 to 102 miles are available. Sag wagon and food stops provided. Visit Active.com to register or call 443-480-4794 or email kneff11@gmail.com for more details.

Art in Bloom

June 24 | 4-6 p.m.

Chestertown RiverArts, 315 High Street, Suite 106, Chestertown

For the fifth year, Chestertown RiverArts and Community Mediation Upper Shore have joined together to produce “Art in Bloom,” a celebration of the art of floral design. Proceeds from Art in Bloom go to support Community Mediation Upper Shore. For more information, call 410-778-6300 or email info@chestertownriverarts.org.

State Championship Junior Sailing Regatta

June 28-29 | 9 a.m.-4 p.m.

RHYC, McKinleyville Road, Rock Hall

This is an annual championship regatta held on the Chesapeake Bay and typically draws 125 to 150+ Optimist, Laser Radial, and C420 sailors and their families and coaches from around the region. For details, call 410-639-2182 or email regattas@rockhallyachtclub.org.

Washington College Riverfront Concert Series

June 28 | 6:30 p.m.

Custom House Lawn, 101 South Water Street, Chestertown

The a cappella sound of Sombarkin: Karen Somerville, Lester Barrett, Jr., and Jerome McKinney, a trio of vocalists whose sound is so well jelled it is amazing to discover just who is singing which part. The group uses the skill of vocal instrumentation and harmony to deliver an explosive performance of Negro spirituals, map (code) songs, folk, gospel, blues, and jazz. Call 410-810-7156 or email mbuckley3@washcoll.edu for the details.

Baby Beauty Contest

June 29 | 6 p.m.

Rock Hall Volunteer Fire Company, Route 20, Rock Hall

Baby beauty contest, with prizes. Call 410-639-7719 or email mparry@rockhallmd.gov to register.

Street Dance

June 29 | 7-9 p.m.

Main Street, Rock Hall

Main Street will be closed to traffic for this street dance. Call 410-639-7719 or email mparry@rockhallmd.gov for more information.

Beach Party

June 30 | 6 p.m.

Public Beach, Rock Hall

Join in the fun with games, music, a bonfire, and to enjoy the beautiful Rock Hall sunset. Call 410-639-7719 or email mparry@rockhallmd.gov for details.

Details

Start:
June 1 @ 8:00 am
End:
June 30 @ 5:00 pm

Venue

Kent County, Maryland
Chestertown, MD 21620 United States + Google Map
Get in Touch

Allison Rogers

Owner/Graphic Designer

allison@attractionmag.com

Attraction Magazine

PO Box 360
Easton, MD 21601

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