Jump to Todays Events


Chestertown Maryland Calendar of Events- May 2024


Login to create a new event.      

May 1

  • MassoniArt presents Spring 2024

  • Wednesday,
  • This event runs April 5 to May 5
  • Location: MassoniArt - High Street - 203 High Street
  • April 5 - May 5

    April First Friday, April 5 5-7pm

    Grace Mitchell, Heidi Fowler, Kathryn O’Grady, Joe Karlik, Blake Conroy, Eve Stockton and gallery artists.

    March, master of winds, brig...

    More information

Baskerville
  • Baskerville

  • Wednesday,   |  Fridays and Saturday- 8p.m. Sundays- 2p.m.
  • This event runs April 19 to May 5
  • Location: Garfield Center for the Arts - 210 High Street
  • Opening April 19 and running through May 5, 2024, is Ken Ludwig’s Sherlock Holmes mystery-comedy “BASKERVILLE.” Ludwig is best known for “Lend Me A Tenor,” “Moon O...

    More information

May 2

Handbuilding with Marcey Sherman
  • Handbuilding with Marcey Sherman

  • Thursday,   |  2-4:30pm
  • Location: Chestertown RiverArts 200B High Street
  • The class will be held at the Clay Studio on Thursdays at 2:00 - 4:30 pm, running from May 2-June 6 (6 weeks).

    For beginning and continuing students. Coils, slabs, and pinch pots. Experience the ba...

    More information

WC Film Series/ Barbie
  • WC Film Series/ Barbie

  • Thursday,   |  7pm
  • Location: Washington College - Norman James Theatre, William Smith Hall
  • Please join us for this month's feature in the WC Film Series, Barbie (2023). Each month, we'll feature a film on the theme of self-discovery. Films will come from a variety of time periods,...

    More information

May 3

Teaching & Transformation: Semester in the Chesapeake Classroom
  • Teaching & Transformation: Semester in the Chesapeake Classroom

  • Friday,   |  4:30 pm - 7:00 pm
  • Location: MuSE: A Community Museum - 210 S Cross Street
  • The first exhibit in this new community museum for MuSE will be “Teaching & Transformation: Semester in the Chesapeake Classroom.” It will showcase the nature and culture of the Chesap...

    More information

May 4

The Magic of Maize
  • The Magic of Maize

  • Saturday,   |  10:00am - 1:00pm
  • Location: Eastern Shore Food Lab (2nd Floor) - Modern Stone Age Kitchen- 236 Cannon Street
  • The powerful ancient process of Nixtamilization is the only way to unlock the maximum amount of nutrients from maize for our bodies.

    Join us and learn how to replicate this ancestral process in you...

    More information

Teaching & Transformation: Semester in the Chesapeake Classroom
  • Teaching & Transformation: Semester in the Chesapeake Classroom

  • Saturday,   |  9:00 am - 11:00 am
  • Location: MuSE: A Community Museum - 210 S Cross Street
  • The first exhibit in this new community museum for MuSE will be “Teaching & Transformation: Semester in the Chesapeake Classroom.” It will showcase the nature and culture of the Chesap...

    More information

May 7

Brampton Inn Ship-To-Shore Experience with Chester River Packet Co.
  • Brampton Inn Ship-To-Shore Experience with Chester River Packet Co.

  • Tuesday,   |  6:00pm - 8:00pm
  • Location: Brampton Inn - 25227 Chestertown Rd
  • The Brampton Inn invites visitors to catch the sunset aboard the Chester River Packet, a 1920’s-style, touring yacht. This immersive experience allows guests to mingle and unwind on a serene two...

    More information

May 9

Walter Pippin Exhibition at the Historical Society
  • Walter Pippin Exhibition at the Historical Society

  • Thursday,   |  Thursday/Friday 11 - 2, Saturday 10 - 1
  • This event runs May 9 to May 11
  • Location: Bordley History Center - 301 High Street
  • An exhibition featuring the architectural work of Chestertown builder Walter T. Pippin

    More information

May 10

  • Emmanuel Episcopal Church Concert Series -- 30th Season

  • Friday,   |  7:30 pm
  • Location: Emmanuel Episcopal Church - Facing the fountain park on Cross Street
  • Ken Cowan. Organist
    Associate Professor and Head of the Organ Program, the Shepherd School of Music, Rice University, Houston, Texas

    More information

Taking Care of your Mother Weekend!
  • Taking Care of your Mother Weekend!

  • Friday,   |  5:00pm - 8:00pm and 10:00am - 1:00pm
  • This event runs May 10 to May 11
  • Location: Eastern Shore Food Lab (2nd Floor) - 236 Cannon Street
  • What better gift for Mother’s Day than a “Taking Care of Your Mother” weekend!

    Friday May 10:
    Arrive at 5:00 and enjoy wood fired pizza and the Sourdough Mother Class (see descri...

    More information

Uncorked Creations Casa Carmen Wine Bottle Planters
  • Uncorked Creations Casa Carmen Wine Bottle Planters

  • Friday,   |  6-8pm
  • Location: Casa Carmen Wines - Casa Carmen Wines, 312 Cannon Street
  • These planters make great gifts during our May Uncorked Creations! Learn how to make a wine bottle planter, all supplies provided including a plant.

    More information

MassoniArt presents Marcy Dunn Ramsey - Transitions
  • MassoniArt presents Marcy Dunn Ramsey - Transitions

  • Friday,
  • Location: MassoniArt - High Street - 203 High Street
  • At the High Street Gallery

    Champagne Reception – Friday, May 10, 5-7 pm
    Open House & Artist Talk – Saturday, May 11, 12-3 pm

    More information

May 11

Mobile Raku One Day Workshop
  • Mobile Raku One Day Workshop

  • Saturday,   |  10am-4pm
  • Location: RiverArts Clay Studio - 204 High Street
  • The class will be held at the Clay Studio on Saturday, May 11 from 10:00 am - 4:00 pm.

    This one-day workshop introduces the fundamentals of raku to students of any experience level. Students will l...

    More information

Teaching & Transformation: Semester in the Chesapeake Classroom
  • Teaching & Transformation: Semester in the Chesapeake Classroom

  • Saturday,   |  9:00 am - 11:00 am
  • Location: MuSE: A Community Museum - 210 S Cross Street
  • The first exhibit in this new community museum for MuSE will be “Teaching & Transformation: Semester in the Chesapeake Classroom.” It will showcase the nature and culture of the Chesap...

    More information

May 12

Elegant Afternoon Tea at Brampton Inn
  • Elegant Afternoon Tea at Brampton Inn

  • Sunday,   |  2:00pm - 3:30pm
  • Location: Brampton Inn - 25227 Chestertown Rd, Chestertown MD 21620
  • Join us on Mother's Day for an exquisite afternoon filled with charm and indulgence at Brampton Inn. Indulge in a delightful selection of finest teas and delectable treats especially curated for ...

    More information

SOLD OUT: Mother's Day Brunch on the River Packet
  • SOLD OUT: Mother's Day Brunch on the River Packet

  • Sunday,   |  12:00 - 2:00 pm
  • Location: River Packet - High Street Town Dock
  • Gather your family/friends to celebrate Mother's Day with a brunch cruise aboard the River Packet! Reservations are required ahead of the sail - click the link for more information and to reserve...

    More information

May 14

Still Life Drawing & Painting Classes
  • Still Life Drawing & Painting Classes

  • Tuesday,   |  9:30 am
  • This event runs May 14 to May 28
  • Location: Diane Rappisi Fine Arts - 241B High Street (enter from Cannon St)
  • Still Life drawing and painting classes on Tuesdays, May 14, 21 and 28. Charcoal drawing in the mornings (9:30-12:30) and painting in the afternoons (1-4pm). All levels welcome. Small classes in a pro...

    More information

May 16

Walter Pippin Exhibition at the Historical Society
  • Walter Pippin Exhibition at the Historical Society

  • Thursday,   |  Thursday/Friday 11 - 2, Saturday 10 - 1
  • This event runs May 16 to May 18
  • Location: Bordley History Center - 301 High Street
  • An exhibition featuring the architectural work of Chestertown builder Walter T. Pippin

    More information

Girls' Night Out on the River Packet
  • Girls' Night Out on the River Packet

  • Thursday,   |  6:00 - 8:00 pm
  • Location: River Packet - High Street Town Dock
  • Ladies' Night on the Chester River! Gather your friends for a fun evening with food and drinks aboard the River Packet. Reservations are required - click the link for more information and to rese...

    More information

Cars on High
  • Cars on High

  • Thursday,   |  6pm-8pm
  • Location: 300 Block of High Street
  • Come show off your favorite car or marvel at other people's pride and joy. This event does not require registration and is free and open to the public....

    More information

May 17

Sophie Kerr Prize Ceremony
  • Sophie Kerr Prize Ceremony

  • Friday,   |  7:30PM
  • Location: Hotchkiss Recital Hall - Gibson Center for the Arts
  • Celebrate the announcement of the Sophie Kerr Prize! Or watch via livestream at: https://youtube.com/live/E_1aNvn4odE?feature=share

    More information

May 18

Women's Ministry
  • Women's Ministry

  • Saturday,   |  10:00am - 11:00am
  • Location: Emmanuel UM Church - 6698 Church Lane
  • Women of God, Working With A Purpose! Join this dynamic women's group as we provide a caring and loving environment that will embrace our spiritual growth while engaging in activities that will ...

    More information

Foraging Fun around Chestertown
  • Foraging Fun around Chestertown

  • Saturday,   |  10:00am - 1:00pm
  • Location: Eastern Shore Food Lab | 2nd Floor | 236 Cannon Street
  • You will never look at your lawn the same way after taking this class!
    Chestertown’s lawns, parks and sidewalks are full of good things to eat, if you know how and where to look.

    You will sp...

    More information

Teaching & Transformation: Semester in the Chesapeake Classroom
  • Teaching & Transformation: Semester in the Chesapeake Classroom

  • Saturday,   |  9:00 am - 11:00 am
  • Location: MuSE: A Community Museum - 210 S Cross Street
  • The first exhibit in this new community museum for MuSE will be “Teaching & Transformation: Semester in the Chesapeake Classroom.” It will showcase the nature and culture of the Chesap...

    More information

May 19

  • Emmanuel Episcopal Church Concert Series -- 30th Season

  • Sunday,   |  2:00 pm
  • Location: Emmanuel Episcopal Church - Facing the fountain park on Cross Street
  • Singing City Choir of Philadelphia, Pennsylvania
    Rollo Dilworth, Director

    More information

  • An Evening Cruise for KART

  • Sunday,   |  6:00PM
  • Location: Chester River Packet - Foot of High Street
  • CHESTER RIVER PACKET

    Light fare and cash bar
    Lite fare provided by Occasions
    $75 Per Person

    Limited number of tickets available

    All proceeds benefit KART

    *Please arrive 15 minutes prior ...

    More information

May 22

Watercolor for Beginners with Denise Dersch
  • Watercolor for Beginners with Denise Dersch

  • Wednesday,   |  10am-3pm
  • Location: RA Classroom 315 High Street
  • Wednesday, May 22 - Thursday, May 23, 2024

    Students will learn choices of watercolor paper, brushes, pigments, importance of values, edges, transparency vs. opacity, and color theory. This class us...

    More information

May 23

Walter Pippin Exhibition at the Historical Society
  • Walter Pippin Exhibition at the Historical Society

  • Thursday,   |  Thursday/Friday 11 - 2, Saturday 10 - 1
  • This event runs May 23 to May 25
  • Location: Bordley History Center - 301 High Street
  • An exhibition featuring the architectural work of Chestertown builder Walter T. Pippin

    More information

Exploration of the Potter's Wheel with Marilee Schumann
  • Exploration of the Potter's Wheel with Marilee Schumann

  • Thursday,   |  6pm-8:30pm
  • Location: RiverArts Clay Studio 200B High Street
  • The class will be held at the Clay Studio from 6:00 - 8:30 pm on Thursdays, May 23 - July 18 (not counting July 4).

    Students will be introduced to wheel techniques and informational context while ...

    More information

  • On-Farm Dinner!

  • Thursday,   |  6:30
  • Location: Oksana's Produce Farm - 2517 McGinnes Road - Oksana's Produce Farm - 2517 McGinnes Road
  • Join us for an On-Farm Dinner! Take a break from the hustle and bustle of daily life to enjoy a beautiful picturesque evening on our farm, where we will take care of YOU for a change! We'll be se...

    More information

May 24

ChestertownTea Party Festival - Block Party
  • ChestertownTea Party Festival - Block Party

  • Friday,   |  5 pm - 9 pm
  • Location: Wilmer Park - Wilmer Park
  • Kick off the Chestertown Tea Party weekend with a good old-fashioned block party. Hosted by Main Street Chestertown, the Block Party features local food trucks, craft beer, a live band, children&rsquo...

    More information

Lands Point Winery Season Opening
  • Lands Point Winery Season Opening

  • Friday,   |  Noon to 7pm
  • Location: Lands Point Winery - 22620 Handy Point Road
  • Lands Point Winery and Vineyards is thrilled to announce our summer opening for the season. We will be open beginning Friday, May 24th and will be open every Friday and Saturday from noon - 7pm (last ...

    More information

May 25

Chestertown Tea Party Festival - Parade
  • Chestertown Tea Party Festival - Parade

  • Saturday,   |  10 AM
  • Location: Downtown Chestertown - Downtown Chestertown
  • Don't miss the parade!
    PARTICIPATE IN THE PARADE


    Start planning your float for the 2024 Chestertown Tea Party Festival! We invite all to participate in the Festival’s popular p...

    More information

Chestertown Tea Party Festival - Reenactment
  • Chestertown Tea Party Festival - Reenactment

  • Saturday,   |  2 PM
  • Location: Downtown Chestertown - Downtown Chestertown
  • In response to British Parliament’s closing of the port of Boston, the citizens of Chestertown, Maryland met in May of 1774 and set forth “Resolves” forbidding importing, selling, or...

    More information

Teaching & Transformation: Semester in the Chesapeake Classroom
  • Teaching & Transformation: Semester in the Chesapeake Classroom

  • Saturday,   |  9:00 am - 11:00 am
  • Location: MuSE: A Community Museum - 210 S Cross Street
  • The first exhibit in this new community museum for MuSE will be “Teaching & Transformation: Semester in the Chesapeake Classroom.” It will showcase the nature and culture of the Chesap...

    More information

  • The CTPDCR and Run for Radcliffe

  • Saturday,   |  8:00 a.m.
  • Location: Wilmer Park - 413 S Cross Street
  • Help us kick off the Chestertown Tea Party Festival on Saturday, May 25th! Hundreds of runners and walkers will race along 5k and 10-mile courses. When you participate in the Run for Radcliffe, you he...

    More information

Music of American Colonies: Anne and Ridley Enslow
  • Music of American Colonies: Anne and Ridley Enslow

  • Saturday,   |  11 am, 1 pm, 3 pm
  • Location: Bordley History Center - 301 High Street
  • Music provides a historical map of time and place. Visit the Bordley History Center during the Tea Party to hear “liberty songs” of the Revolutionary War and other music of the American co...

    More information

May 26

Chestertown Tea Party Festival - Beer Fest
  • Chestertown Tea Party Festival - Beer Fest

  • Sunday,   |  Noon - 4 PM
  • Location: Wilmer Park - Wilmer Park
  • On Sunday, the festivity continues at Wilmer Park beginning at noon, with the 3rd annual Beer Fest, live music, food trucks, craft vendors, plenty of fun for families- a Punch & Judy show, instru...

    More information

Chestertown Tea Party Festival - Raft Race
  • Chestertown Tea Party Festival - Raft Race

  • Sunday,   |  2:30 PM
  • Location: Wilmer Park/Chester River - Wilmer Park/Chester River
  • Annually, at 2:30 PM on Sunday of Chestertown’s Tea Party Festival, the Raft Race attracts hundreds of spectators to an unusual event- a race of rafts made of non-nautical materials on the Chest...

    More information

May 27

Memorial Day Lunch Cruise on the River Packet
  • Memorial Day Lunch Cruise on the River Packet

  • Monday,   |  12:00 - 2:00 pm
  • Location: River Packet - High Street Town Dock
  • Gather your family and friends on Memorial Day for a lunch cruise on the Chester River! Reservations are required - click the link for more information and to reserve your tickets!...

    More information

May 29

Chestertown Open Mic
  • Chestertown Open Mic

  • Wednesday,   |  7:30PM
  • Location: Garfield Theater
  • OPEN MIC at THE GARFIELD! The last Wednesday of each month.

    PARTICIPANTS and SPECTATORS wanted!!
    Contact Ford Schumann at Schumannford@gmail.com to participate.

    Refreshments available for pur...

    More information