Join us December 3-5, 2021 for the 4th Annual Dickens of a Christmas in downtown Chestertown. Chestertown’s beautiful architecture is the backdrop for a lively London-themed weekend filled with Victorian entertainment, food, shopping, children’s activities, and more. Make sure to follow us on Facebook for the most up-to-date information. For more info and schedule of… Continue Reading Dickens of a Christmas

5-7pm Friday, 10-5pm Sat., 11-3pm Sun. This is a community event that allows the community for all ages to visit a display of trees decorated by businesses, organizations as well as families. This is our way of saying thank you to the community for helping Soroptimist with the betterment of women and girls. Our Christmas… Continue Reading Festival of Trees Weekend

Annual RiverArts Holiday Show & Sale Something for every pocketbook! These unique & beautifully crafted handmade gifts created by our member artisans include everything from clothing to fashion accessories, jewelry, home and holiday décor, stocking stuffers, holiday cards and ornaments, original paintings and more!

In Meghan Efland's backyard, near downtown Chestertown & Washington College (When you register, you'll receive a confirmation email with Meghan's address.) Cost: $35 Join us for camaraderie & creativity as we make festive holiday decor that will brighten your home or make a perfect gift! Meghan started making holiday wreaths with her grandmother, mother, and… Continue Reading December 5: Holiday Wreath Making

Get your Christmas shopping done early and enjoy some wine while you do it! A wide variety of vendors will be at Broken Spoke, Chateau Bu De & Crow Vineyard so you can shop for local gifts for family, friends, and of course to treat yourself! A list of vendors will be updated as they… Continue Reading Rivers to Canal Holiday Sip & Shop

DECEMBER 3 – 19, 2021 Music by Jeanine Tesori, Book & Lyrics by David Lindsay-Abaire Directed by Jennifer Kafka Smith FAMILY FRIENDLY SHOW TIMES! Fridays & Saturdays @ 7pm Sundays @ 2pm Thank you to our Presenting Sponsor: Chesapeake Bank and Trust

Grab your knickers and kick off your holiday season in true Dickens fashion as you savor an authentic Victorian Dining experience at the Modern Stone Age Kitchen. Like a virtual time machine, you'll explore the history, culture and atmosphere of the Victorian era through a lavish, multi-course Christmas dinner as it would have been prepared… Continue Reading A Victorian Dining Experience

7/27/2021 - The Town Council voted to change the meeting start time to 6:30pm moving forward CLICK FOR TOWN AGENDAS & MINUTES

8/16/2021 - The Town Council is following CDC guidelines and request that all attendees wear masks regardless of vaccination status. 7/27/2021 - The Town Council voted to change the meeting start time to 6:30pm moving forward 7/14/2021 - Town meetings are resuming in Town Hall and are open to the public.  Meetings will still be… Continue Reading Mayor and Council Meeting

Opening the 2022 season at the Garfield Center for the Arts in February is the over-the-top hilarious new comedy The Play That Goes Wrong, by Henry Lewis, Jonathan Sayer and Henry Shields. The Garfield Center’s Executive Director, Steven Arnold, will direct the production. Auditions are scheduled for Saturday, December 4th 2021 from 2:00 to 5:00… Continue Reading OPEN AUDITIONS – The Play That Goes Wrong

2021 Holiday Exhibition December 2021 – January 2022 New work by Gallery Artists and special guests. I lift up my eyes to the mountains –       where does my help come from? Psalm 121:1-2 Featured at High Street: Katherine Cox | Wendy Prellwitz | Grace Mitchell | Heidi Fowler | Greg Mort | Michael Kahn |… Continue Reading MassoniArt 2021 Holiday Exhibition

Annual RiverArts Holiday Show & Sale Something for every pocketbook! These unique & beautifully crafted handmade gifts created by our member artisans include everything from clothing to fashion accessories, jewelry, home and holiday décor, stocking stuffers, holiday cards and ornaments, original paintings and more!

Opening the 2022 season at the Garfield Center for the Arts in February is the over-the-top hilarious new comedy The Play That Goes Wrong, by Henry Lewis, Jonathan Sayer and Henry Shields. The Garfield Center’s Executive Director, Steven Arnold, will direct the production. Auditions are scheduled for Saturday, December 4th 2021 from 2:00 to 5:00… Continue Reading OPEN AUDITIONS – The Play That Goes Wrong

Annual RiverArts Holiday Show & Sale Something for every pocketbook! These unique & beautifully crafted handmade gifts created by our member artisans include everything from clothing to fashion accessories, jewelry, home and holiday décor, stocking stuffers, holiday cards and ornaments, original paintings and more!

2021 Holiday Exhibition December 2021 – January 2022 New work by Gallery Artists and special guests. I lift up my eyes to the mountains –       where does my help come from? Psalm 121:1-2 Featured at High Street: Katherine Cox | Wendy Prellwitz | Grace Mitchell | Heidi Fowler | Greg Mort | Michael Kahn |… Continue Reading MassoniArt 2021 Holiday Exhibition

DECEMBER 3 – 19, 2021 Music by Jeanine Tesori, Book & Lyrics by David Lindsay-Abaire Directed by Jennifer Kafka Smith FAMILY FRIENDLY SHOW TIMES! Fridays & Saturdays @ 7pm Sundays @ 2pm Thank you to our Presenting Sponsor: Chesapeake Bank and Trust

UPDATE 3/23/2021 - The full season of the Chestertown Farmers and Artisans Market opens Saturday, March 27 and will continue to the week leading up to Christmas. Artisans, who are back after the winter pause, and new and returning farm vendors will be set up from 8 a.m. to noon every Saturday in the 200… Continue Reading Chestertown Farmers Market

Come to the Chestertown Arts & Entertainment District’s HOLIDAY ART WALK. Dozens of artists and artisans will be selling works at galleries, storefronts, restaurants and a pop- up venue at the BANK (211 High St). For information email chestertownae@gmail.com or call the Kent Cultural Alliance at 410-778-3700

If you’re nostalgic for toy trains or mesmerized by model railroads, be sure to mark your calendar for Kent County Public Library’s Toy Train & Model Railroad Expo! Bob and David Singer have spent decades collecting and curating magnificent operating layouts featuring tinplate trains from bygone eras. It is a joy to share their enthusiasm… Continue Reading 8th Annual Toy Train & Model Railroad Expo

2021 Holiday Exhibition December 2021 – January 2022 New work by Gallery Artists and special guests. I lift up my eyes to the mountains –       where does my help come from? Psalm 121:1-2 Featured at High Street: Katherine Cox | Wendy Prellwitz | Grace Mitchell | Heidi Fowler | Greg Mort | Michael Kahn |… Continue Reading MassoniArt 2021 Holiday Exhibition

Annual RiverArts Holiday Show & Sale Something for every pocketbook! These unique & beautifully crafted handmade gifts created by our member artisans include everything from clothing to fashion accessories, jewelry, home and holiday décor, stocking stuffers, holiday cards and ornaments, original paintings and more!

Dear Teens, You are cordially invited to an afternoon of fine pizza and even finer hot chocolate charcuterie. Feast on delicious treats in the library and create your own mini hot chocolate board to share with friends and family. All supplies will be provided and will range from chocolates, candies, marshmallows, pops, cookies, and more!… Continue Reading Hot Chocolate Boards – A Pizza and Make A Thing Event

December 11 @ 4:00 pm - 7:00 pm$18 /per person $15 /Wine Club Join us this holiday season for the lighting of the vineyard. Ticket includes a glass of featured wine. We will have hayrides around the vineyard and bonfires to keep you warm. Join in with the carolers as they sing in the holiday… Continue Reading Lighting of the Vineyard

DECEMBER 3 – 19, 2021 Music by Jeanine Tesori, Book & Lyrics by David Lindsay-Abaire Directed by Jennifer Kafka Smith FAMILY FRIENDLY SHOW TIMES! Fridays & Saturdays @ 7pm Sundays @ 2pm Thank you to our Presenting Sponsor: Chesapeake Bank and Trust