Vendor Events in Chestertown, MDVendor Events in Chestertown, MD
3 farmers markets, craft fairs, festivals, and pop-ups in Chestertown, MD. Find booth fees, open spots, and apply to sell.3 upcoming.
As of October 29, 2026, VendorsMap lists 3 upcoming farmers markets, craft fairs, festivals and pop-ups in Chestertown, MD. Each listing says how to apply where the organizer published it. 1 of those lists a booth fee. None of them lists an application deadline still ahead.
Different Chestertown? Chestertown, NY
2festivals
1farmers market
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In Chestertown
Soonest first
Chestertown Farmers Market
Chestertown · Saturdays
Paint the Town
Chestertown · Thu-Mon, Apr 22-26
Chestertown Tea Party Festival
Chestertown · Sun-Mon, May 23-24
Takes about 30 seconds.
An account takes about 30 seconds.
Upcoming shows taking vendors
Week of Apr 19
Thursday April 22 to Sunday April 25Apr 22 to 25
DateShowTypeBooth fee · Deadline
APR22-26
Paint the Town
Chestertown, MD · Thu-Mon
ChestertownFestival
Annual spring festival in historic Chestertown featuring local artists, crafts, and community celebration in April.
Fee Ask organizer
Festival
Ask organizer · No deadline listed
DetailsHear about new Chestertown shows first.
Your account alerts you when a show near you starts taking vendors, and keeps your applications in one place.Takes about 30 seconds.
Takes about 30 seconds. Join 65,700+ vendors.
Week of May 17
Sunday May 23May 23
DateShowTypeBooth fee · Deadline
MAY23-24
Chestertown Tea Party Festival
Chestertown, MD · Sun-Mon
ChestertownFestival
The Chestertown Tea Party Festival is a memorial day weekend event celebrating the town's colonial history with a major artisan market component. The festival features over 100...
Fee From $125
Festival
From $125 · No deadline listed
DetailsWeekly & monthly marketsWeekly markets
Regular dates you can build a season aroundFarmers Markets in Chestertown (1)
Festivals in Chestertown (2)
Festival
Paint the Town
by Paint the Town
Chestertown, Maryland
April 22-26, 2027
Annual spring festival in historic Chestertown featuring local artists, crafts, and community celebration in April.
Festival$125 craft vendor; $225 food vendor
Chestertown Tea Party Festival
by Chestertown Tea Party Festival Inc.
Downtown Chestertown, High St, Chestertown, MD 21620
May 23-24, 2027 (expected)
The Chestertown Tea Party Festival is a memorial day weekend event celebrating the town's colonial history with a major artisan market component. The festival features over 100...
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Run a market or fair in Chestertown?
Questions vendors ask
Where can I sell as a vendor in Chestertown, MD?
VendorsMap lists 3 upcoming vendor events in Chestertown, MD. By kind: 2 festivals, 1 farmers market. The most listings are in Chestertown (3). Every listing shows its dates, location, booth fee and deadline where the organizer published them.
How much are booth fees for vendor events in Chestertown, MD?
1 of the 3 upcoming vendor events in Chestertown, MD lists a booth fee. The one clear price listed is $125. The rest describe their fees in their own words or ask vendors to contact them; each listing shows what the organizer wrote.
Which vendor events in Chestertown, MD are coming up next?
3 are coming up. Check each listing for how to apply. The soonest: Chestertown Farmers Market in Chestertown (Year-round, every Saturday...); Paint the Town in Chestertown (Apr 22-26); Chestertown Tea Party Festival in Chestertown (May 23-24). The full list, soonest first, is on this page.
When are the next vendor application deadlines in Chestertown, MD?
None of the upcoming vendor events in Chestertown, MD publishes a deadline still ahead. Check each listing and ask the organizer before you plan around a date.
How do I apply to sell at a market or fair in Chestertown, MD?
Open the listing to check its dates, booth fee and deadline, then apply. For the others, the listing links to the organizer's own application so you can apply externally. A free VendorsMap account keeps your applications in one place and alerts you when new vendor events near you open.
Do I need an account to find vendor events on VendorsMap?
No. Every listing in Chestertown, with its booth fee, deadline and application link, is open to browse. Optional membership adds first-access alerts a day before everyone else when new Chestertown events are approved, and puts your applications at the top of the organizer's list.
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The whole city
See all 3 Chestertown shows on one map.
Every farmers market, craft fair, festival and pop-up taking vendors. Tap a pin for dates. Fees and deadlines are on each one.
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