Chestertown: The County Seat of Kent County

Arts and entertainment fuel this Bohemian town in Maryland.



Making your way back to Md. 213, continue south to Chestertown. The county seat of Kent County, the town’s historic roots go back before the Revolutionary War. George Washington himself passed through the town many times going to and from Philadelphia, and Washington College takes its name from him. 

Stop at the visitor’s center at Md. 213 and Cross Street and pick up information on shops and attractions (chestertown.com). Make sure you take the walking tour (map provided at the visitor’s center), which includes many historic buildings and restored residences—some now repurposed into myriad shops, antiques stores (including a “gently used” bookstore on South Cross Street, The Bookplate), restaurants and artists’ galleries. An architectural guide is available online.

Several artists have working studios in town. Check out First Fridays in Chestertown, when shops, antiques stores and galleries are open late and special arts and entertainment are offered. 

Garfield Center for the Arts at the Prince Theatre on High Street has a packed schedule of plays, lectures and special events. Combine theater with lunch or dinner at the Imperial Inn and Restaurant next door. 

Discover the taste of old world breads at Evergrain Bread Company on High Street, featuring organic, artisan-crafted whole-grain breads and pastries. Everything is baked the night before to ensure freshness. Soups, sandwiches and drinks are also available—it’s a place enjoyed by locals and visitors alike. 

At the center of town is Fountain Park, at High and Cross streets, with an ornate working fountain standing at its heart. Chestertown Farmers Market and the Artisans Market operate there every Saturday morning 8 a.m. to noon from March through December, with limited operation in the winter. Local growers and artisans offer fresh flowers, meats, cheese and vegetables, artwork and products like natural soaps, baskets and other crafts. Concerts and special events also take place at the park throughout the warm months.

Other events and activities throughout the year include an historic house tour, the annual Tea Party, a waterfront Tall Ship Festival and the county-wide Chestertown River Arts Studio Tour and Show.

Highlights not to miss: 

  • The schooner Sultana, based at the town’s waterfront at the end of High Street. Sultana is a replica of a pre-Revolutionary War British schooner. Day-long educational programs are available through the Sultana education program, including canoeing and kayaking. 
  • Chestertown RiverArts is a community arts center on High Street with ongoing exhibits and classes throughout the year for adults and children in painting, sculpture, fiber, mixed media, clay and more. 
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January 2017

January 3 - 28  “Winter Group Show” Rotating Group Show features a variety of art in different styles and media. Custom Framing & Gift Certificates are always available. Gallery Hours:...

Cost: free

Where:
The Station Gallery
3922 Kennett Pike
Greenville, DE  19807
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Telephone: 302-654-8638
Website »

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Sports Card & Collectible Show at Aetna Fire Hall on Jan. 22—sign up now! -Sports Cards McFarlane Figures Comic Books Non-Sports cards Wrestling Items Vintage Starting...

Cost: $2

Where:
Aetna Fire Hall
400 Ogletown Road
Newark, DE  19711
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Sponsor: A2Z Promotions
Telephone: 302-983-2636
Contact Name: Bob Harper
Website »

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The Rehoboth Beach Film Society announces the next play in the exciting series of National Theatre Live screenings. National Theatre Live is a groundbreaking project that presents the best of...

Cost: $18-$20

Where:
Cinema Art Theater
17701 Dartmouth Drive, #2
Lewes, DE  19958
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Sponsor: Rehoboth Beach Film Society
Telephone: 302-645-9095
Contact Name: Jeri Kaplan
Website »

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Belly Dance Classes with Zahra Beginner & intermediate classes open to teens and adults Sundays in January starting Jan 8th Beginner: 2:30-3:30 p.m. Intermediate: 1 - 2 p.m (must get...

Cost: $15-$42

Where:
Take the Lead Studio
320 Lantana Drive
Hockessin , DE  19711
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Sponsor: Take the Lead
Contact Name: Zahra
Website »

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The Resident Ensemble Players, Delaware’s professional acting company performing at the University of Delaware, presents The Bells by Theresa Rebeck. During the great Yukon gold rush of the...

Cost: $15 - $30

Where:
Thompson Theatre, Roselle Center for the Arts
110 Orchard Rd.
Newark, DE  19716
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Sponsor: Resident Ensemble Players
Telephone: (302) 831-2204
Website »

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Ah, typecasting—the baritone is always the bad guy! In Devils, Drunks & Dastardly Dudes, we’ll go on an operatic journey of men behaving badly. We’ll add a tenor to the mix, too… but we...

Cost: $29-$59

Where:
OperaDelaware Studio
4 South Poplar St.
Wilmington, DE  19801
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Sponsor: OperaDelaware
Telephone: 302-442-7809
Contact Name: Mary Wilcosky
Website »

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Come give curling a try! At this 2-hour intro-to-curling event we'll provide a basic lesson then coach you through a mini-game.  Whether you just want to cross #curling off your bucket list or...

Cost: $35

Where:
The Pond Ice Arena
101 John Campbell Rd
Newark, DE  19711
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Sponsor: Diamond State Curling Club
Website »

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January 3 - 28  “Winter Group Show” Rotating Group Show features a variety of art in different styles and media. Custom Framing & Gift Certificates are always available. Gallery Hours:...

Cost: free

Where:
The Station Gallery
3922 Kennett Pike
Greenville, DE  19807
View map »


Telephone: 302-654-8638
Website »

More information

The Rehoboth Beach Film Society announces the next play in the exciting series of National Theatre Live screenings. National Theatre Live is a groundbreaking project that presents the best of...

Cost: $18-$20

Where:
Cinema Art Theater
17701 Dartmouth Drive, #2
Lewes, DE  19958
View map »


Sponsor: Rehoboth Beach Film Society
Telephone: 302-645-9095
Contact Name: Jeri Kaplan
Website »

More information

Notbybreadalone Ministries presents Feeding the Hungry Outreach. All are welcome to come and partake of food, fun and fellowship. Those who desire a better way of life through Jesus Christ are...

Cost: Free

Where:
2nd and 3rd Streets
Wilmington, DE  19801


Sponsor: Notbybreadalone Outreach Ministries
Telephone: 442-0440
Contact Name: Ministers Wayne and Stephanie Dumpson
Website »

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Guest speakers Patty Dailey-Lewis, executive director of the Beau Biden Foundation, and Delaware Family Court commissioner Loretta Young will discuss how participation in social media can too...

Cost: Free

Where:
Wilmington University - Dover
Building A Auditorium
3282 N DuPont Highway
Dover, DE  19901
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Sponsor: Wilmington University College of Social & Behavioral Sciences
Telephone: 302-295-1164
Contact Name: Dr. Johanna Bishop
Website »

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January 3 - 28  “Winter Group Show” Rotating Group Show features a variety of art in different styles and media. Custom Framing & Gift Certificates are always available. Gallery Hours:...

Cost: free

Where:
The Station Gallery
3922 Kennett Pike
Greenville, DE  19807
View map »


Telephone: 302-654-8638
Website »

More information

Tuesdays and Thursdays from 9:30AM-12:00PM Fall session: Thursday, Dec 1st thru Thursday, December 15th Winter session: Tuesday, January 17th thru Thursday, March 30th   Drop in on Nature is...

Cost: see description

Where:
The Annex
501 Chandler Mill Rd
Kennett Square, PA  19348
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Sponsor: The Land Conservancy
Telephone: 610-347-0347 ext.104
Website »

More information

East Coast Garden Center Indoor Farmers Market Nov 8, 2016 - April 11, 2017  11 am- 2 pm 25 vendors Location:  East Coast Garden Center 30366 Cordrey Rd Millsboro, DE 19966 302-945-3489

Cost: frr

Where:
East Coast Garden Center
30366 Cordrey Rd
Millsboro, DE  19966
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Sponsor: East Coast Garden Center
Telephone: 302-945-3489
Website »

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East Coast Garden Center Indoor Farmer's Marke 25 vendors

Cost: Free

Where:
East Coast Garden Center
30366 Cordrey Rd
Millsboro, DE  19966
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Telephone: 302-945-3489
Website »

More information

The Rehoboth Beach Film Society announces the next play in the exciting series of National Theatre Live screenings. National Theatre Live is a groundbreaking project that presents the best of...

Cost: $18-$20

Where:
Cinema Art Theater
17701 Dartmouth Drive, #2
Lewes, DE  19958
View map »


Sponsor: Rehoboth Beach Film Society
Telephone: 302-645-9095
Contact Name: Jeri Kaplan
Website »

More information

A four-week series of ballroom dancing classes taught by teachers from the BlueBallroom. Tuesdays starting Jan. 10. Classes are $30 a lesson for Non-Members. Non-Member slots are limited. For...

Cost: $30

Where:
University and Whist Club
805 N Broom St
Wilmington, DE  19806
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January 3 - 28  “Winter Group Show” Rotating Group Show features a variety of art in different styles and media. Custom Framing & Gift Certificates are always available. Gallery Hours:...

Cost: free

Where:
The Station Gallery
3922 Kennett Pike
Greenville, DE  19807
View map »


Telephone: 302-654-8638
Website »

More information

The Rehoboth Beach Film Society announces the next play in the exciting series of National Theatre Live screenings. National Theatre Live is a groundbreaking project that presents the best of...

Cost: $18-$20

Where:
Cinema Art Theater
17701 Dartmouth Drive, #2
Lewes, DE  19958
View map »


Sponsor: Rehoboth Beach Film Society
Telephone: 302-645-9095
Contact Name: Jeri Kaplan
Website »

More information

Show More...
Show Less...

January 3 - 28  “Winter Group Show” Rotating Group Show features a variety of art in different styles and media. Custom Framing & Gift Certificates are always available. Gallery Hours:...

Cost: free

Where:
The Station Gallery
3922 Kennett Pike
Greenville, DE  19807
View map »


Telephone: 302-654-8638
Website »

More information

Tuesdays and Thursdays from 9:30AM-12:00PM Fall session: Thursday, Dec 1st thru Thursday, December 15th Winter session: Tuesday, January 17th thru Thursday, March 30th   Drop in on Nature is...

Cost: see description

Where:
The Annex
501 Chandler Mill Rd
Kennett Square, PA  19348
View map »


Sponsor: The Land Conservancy
Telephone: 610-347-0347 ext.104
Website »

More information

Thursdays from 4:00PM-5:30PM Fall session: December 1st, 8th and 15th Winter session: Starts January 19th, every other Thursday until March 30th This program is based entirely outdoors and is...

Cost: Cost: $30 for TLC members / $40 for non-members

Where:
Bucktoe Creek Preserve
432 Sharp Rd
Avondale, PA  19311
View map »


Sponsor: The Land Conservancy
Telephone: 610-347-0347 ext.104
Website »

More information

MARC BROUSSARD In 2004, Marc Broussard, then a precocious 22-year-old singer/songwriter, released his major-label debut; he called it Carencro, after the Louisiana town where he was born and...

Cost: $22 SRO- $32 SEATED

Where:
World Cafe Live Wilmington
500 N Market St
Wilmington, DE  19801
View map »


Telephone: 215-222-1400
Contact Name: MP Intern
Website »

More information

The Resident Ensemble Players, Delaware’s professional acting company performing at the University of Delaware, presents The Bells by Theresa Rebeck. During the great Yukon gold rush of the...

Cost: $15 - $30

Where:
Thompson Theatre, Roselle Center for the Arts
110 Orchard Rd.
Newark, DE  19716
View map »


Sponsor: Resident Ensemble Players
Telephone: (302) 831-2204
Website »

More information

Show More...
Show Less...

January 3 - 28  “Winter Group Show” Rotating Group Show features a variety of art in different styles and media. Custom Framing & Gift Certificates are always available. Gallery Hours:...

Cost: free

Where:
The Station Gallery
3922 Kennett Pike
Greenville, DE  19807
View map »


Telephone: 302-654-8638
Website »

More information

Tutto Fresco has live entertainment every Friday night from 6:30–9:30 p.m. Call for details. http://tuttofrescode.com/

Where:
Tutto Fresco
514 Philadelphia Pike
Wilmington, DE  19809
View map »

More information

The Resident Ensemble Players, Delaware’s professional acting company performing at the University of Delaware, presents The Bells by Theresa Rebeck. During the great Yukon gold rush of the...

Cost: $15 - $30

Where:
Thompson Theatre, Roselle Center for the Arts
110 Orchard Rd.
Newark, DE  19716
View map »


Sponsor: Resident Ensemble Players
Telephone: (302) 831-2204
Website »

More information

Meeting every Friday, Bayhealth Kent General Hospital, 640 s. State Street, Dover, 7:30 pm., Private Dining Room #3 in the basement. For those who have, or think they may have a gambling problem....

Cost: 0.00

Where:
Bayhealth Kent General Hospital
640 S. State Street
Private Dining Room #3
Dover, DE  19901
View map »


Telephone: 800-855-2CALLGA
Website »

More information

Cost: $12-$20

Where:
Wilmington Drama League
10 West Lea Blvd.
Wilmington, DE  19802
View map »


Sponsor: Wilmington Drama League
Telephone: 302-764-3396
Contact Name: Kathy Buterbaugh
Website »

More information

Show More...
Show Less...

January 3 - 28  “Winter Group Show” Rotating Group Show features a variety of art in different styles and media. Custom Framing & Gift Certificates are always available. Gallery Hours:...

Cost: free

Where:
The Station Gallery
3922 Kennett Pike
Greenville, DE  19807
View map »


Telephone: 302-654-8638
Website »

More information

January 28 – Saturday – 1 to 4 p.m. Science Saturday – Truss Me, You Won’t Fall! Become an engineer for the day. Design a bridge to hold as much weight as possible....

Cost: Activities are included in regular admission and free for members.

Where:
Hagley Museum
201 Hagley Creek Road
Wilmington, DE  19807
View map »


Sponsor: Hagley Museum
Telephone: (302) 65802400 x 238
Contact Name: Jessica Eisenbrey
Website »

More information

The Resident Ensemble Players, Delaware’s professional acting company performing at the University of Delaware, presents The Bells by Theresa Rebeck. During the great Yukon gold rush of the...

Cost: $15 - $30

Where:
Thompson Theatre, Roselle Center for the Arts
110 Orchard Rd.
Newark, DE  19716
View map »


Sponsor: Resident Ensemble Players
Telephone: (302) 831-2204
Website »

More information

GRILLED CHEESE AND CRAFT BEER TASTING We have taken two of the best things on earth and paired them together – Grilled Cheese and Craft Beer – and paired them together in unexpected and...

Cost: $40

Where:
World Cafe Live Wilmington
500 N Market St
Wilmington, DE  19801
View map »


Telephone: 215-222-1400
Contact Name: MP Intern
Website »

More information

Saturday, January 28, 2017 at  7:30 pm at St. David’s Episcopal Church, 763 Valley Forge Rd, Wayne, PA 19087 Sunday, January 29, 2017 at 3 pm at Church of the Holy Trinity, Rittenhouse Square...

Cost: Tickets are $25 online, and $30 at the door. Student tickets $10 at the door.

Where:
Church of the Holy Trinity
1904 Walnut St.
Philadelphia, PA  19103
View map »


Sponsor: Lyric Fest
Telephone: 215-438-1702
Contact Name: Jessica Nelson
Website »

More information

Fan favorite, Dick Smith, returns to the Dickinson Theatre Organ Society concert stage on Saturday, Jan. 28, 2017 for a show that is sure to bring the house down! Dick Smith has been a...

Cost: $15 Adults; $10 Students

Where:
John Dickinson High School Auditorium
1801 Milltown Road
Wilmington, DE  19808
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Sponsor: Dickinson Theatre Organ Society
Telephone: 302-995-2603
Contact Name: Bob Dilworth
Website »

More information

The Dickinson Theatre Organ Society presents Dick Smith. For tickets, click here: http://www.dtoskimball.org/events-tickets/ticket-information/ For further information, please call us at...

Where:
, DE

More information

The Resident Ensemble Players, Delaware’s professional acting company performing at the University of Delaware, presents The Bells by Theresa Rebeck. During the great Yukon gold rush of the...

Cost: $15 - $30

Where:
Thompson Theatre, Roselle Center for the Arts
110 Orchard Rd.
Newark, DE  19716
View map »


Sponsor: Resident Ensemble Players
Telephone: (302) 831-2204
Website »

More information

Cost: $12-$20

Where:
Wilmington Drama League
10 West Lea Blvd.
Wilmington, DE  19802
View map »


Sponsor: Wilmington Drama League
Telephone: 302-764-3396
Contact Name: Kathy Buterbaugh
Website »

More information

MOTHERSHIP Mothership is the area's premier Led Zeppelin Tribute show. Composed of seasoned, professional musicians Mario Padovani - vocals, keyboards, Frank Ginocchio - drums, Chris Julian -...

Cost: 15

Where:
World Cafe Live Wilmington
500 N Market St
Wilmington, DE  19801
View map »


Telephone: 215-222-1400
Website »

More information

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