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Festivals in Chestertown, MD

Search for something you love or check out popular events in your area.

MPB - Middle River Lighted Boat Parade-Family Friendly
Sat, Nov 29, 4:00 PM
Essex · Maryland Party Boat Charters
MPB - Middle River Lighted Boat Parade-Family Friendly
Sat, Nov 29, 4:00 PM
Essex · Maryland Party Boat Charters
Just added!
The Havre De Grace Christmas Spectacular Presented by the STAR Centre
Fri, Dec 12, 8:00 PM
Havre de Grace · The STAR Centre
Just added!
The Havre De Grace Christmas Spectacular Presented by the STAR Centre
Fri, Dec 12, 8:00 PM
Havre de Grace · The STAR Centre
Pretty in Pink | Women-Owned Business Holiday Market
Sat, Dec 6, 11:00 AM
Middletown · St. Anne's Golf Links
Pretty in Pink | Women-Owned Business Holiday Market
Sat, Dec 6, 11:00 AM
Middletown · St. Anne's Golf Links
Selling quickly
2026 Spring Craft Fair
Sat, Mar 21, 10:00 AM
Pasadena · Chesapeake High School
Selling quickly
2026 Spring Craft Fair
Sat, Mar 21, 10:00 AM
Pasadena · Chesapeake High School
Thanksgiving In The Tank Room
Thu, Nov 27, 10:00 AM + 1 more
Chesapeake City · 237 Bohemia Manor Farm Ln
Thanksgiving In The Tank Room
Thu, Nov 27, 10:00 AM + 1 more
Chesapeake City · 237 Bohemia Manor Farm Ln
VENDORS WANTED! Baltimore Pop Up Shop 2025
Sat, Dec 6, 2:00 PM
Baltimore · The A Experience Lifestyle Lounge
VENDORS WANTED! Baltimore Pop Up Shop 2025
Sat, Dec 6, 2:00 PM
Baltimore · The A Experience Lifestyle Lounge
Christmas in Odessa 2025 • 61st Anniversary
Sat, Dec 6, 10:00 AM
Odessa · 201 Main St
Christmas in Odessa 2025 • 61st Anniversary
Sat, Dec 6, 10:00 AM
Odessa · 201 Main St
Annapolis Chocolate Binge Festival 2025
Sun, Dec 7, 11:00 AM
Annapolis · 53 West St
Annapolis Chocolate Binge Festival 2025
Sun, Dec 7, 11:00 AM
Annapolis · 53 West St
Selling quickly
Baltimore Taco Festival
Tomorrow at 2:00 PM
Baltimore · Power Plant Live!
Selling quickly
Baltimore Taco Festival
Tomorrow at 2:00 PM
Baltimore · Power Plant Live!
Town Square Perry Hall Health & Wellness Fair
Sat, Apr 11, 12:00 PM
Baltimore · 9708 Belair Rd
Town Square Perry Hall Health & Wellness Fair
Sat, Apr 11, 12:00 PM
Baltimore · 9708 Belair Rd
Just added!
Franklin Street Holiday Market @ La Banque de Fleuve
Sat, Dec 13, 11:00 AM
Havre de Grace · La Banque de Fleuve-Wedding Reception Venue
Just added!
Franklin Street Holiday Market @ La Banque de Fleuve
Sat, Dec 13, 11:00 AM
Havre de Grace · La Banque de Fleuve-Wedding Reception Venue
2025 Baltimore Crown Awards: Celebrating 19 Years of The Baltimore Scene
Sun, Dec 7, 7:00 PM
Baltimore · 316 Guilford Ave
2025 Baltimore Crown Awards: Celebrating 19 Years of The Baltimore Scene
Sun, Dec 7, 7:00 PM
Baltimore · 316 Guilford Ave
Sales end soon
THE BLACK MALL SUNDAY - (Bmore's Love Market)
Sunday at 1:00 PM
Baltimore · The Black Mall
Sales end soon
THE BLACK MALL SUNDAY - (Bmore's Love Market)
Sunday at 1:00 PM
Baltimore · The Black Mall
Youth Christmas Craft Fair
Tue, Dec 23, 11:00 AM
Baltimore · 901 N Milton Ave
Youth Christmas Craft Fair
Tue, Dec 23, 11:00 AM
Baltimore · 901 N Milton Ave
DE Beer Wine and Spirits Showcase
Sat, Mar 7, 4:00 PM
Dover · Delaware Agricultural Museum
DE Beer Wine and Spirits Showcase
Sat, Mar 7, 4:00 PM
Dover · Delaware Agricultural Museum
93rd Annual Dover Days Festival - Vendor & Parade Registration
Fri, May 1, 5:00 PM
Dover · The Green
93rd Annual Dover Days Festival - Vendor & Parade Registration
Fri, May 1, 5:00 PM
Dover · The Green
Beer Diploma at Christmas Village in Baltimore - Meet the Brewer
Wed, Dec 3, 5:00 PM + 14 more
Baltimore · 501 Light Street, Baltimore, Maryland, USA
Beer Diploma at Christmas Village in Baltimore - Meet the Brewer
Wed, Dec 3, 5:00 PM + 14 more
Baltimore · 501 Light Street, Baltimore, Maryland, USA
Thirsty Thursday Wine Tastings at Christmas Village in Baltimore
Thu, Dec 4, 5:00 PM + 14 more
Baltimore · 501 Light Street, Baltimore, Maryland, USA
Thirsty Thursday Wine Tastings at Christmas Village in Baltimore
Thu, Dec 4, 5:00 PM + 14 more
Baltimore · 501 Light Street, Baltimore, Maryland, USA
The Masters Ceremony
Fri, Nov 21, 6:00 PM + 3 more
Baltimore · AREA 405
The Masters Ceremony
Fri, Nov 21, 6:00 PM + 3 more
Baltimore · AREA 405
Kee's Cookies & Cupcakes Dessert Wars
Sat, Mar 28, 12:00 PM
Dover · Bally's Dover Casino Resort
Kee's Cookies & Cupcakes Dessert Wars
Sat, Mar 28, 12:00 PM
Dover · Bally's Dover Casino Resort

Trends in Chestertown

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Explore more trends

Frequently asked questions about Chestertown

What are the best festival events to attend?

According to Eventbrite, the best festival events are:

MPB - Middle River Lighted Boat Parade-Family Friendly

The Havre De Grace Christmas Spectacular Presented by the STAR Centre

Pretty in Pink | Women-Owned Business Holiday Market

2026 Spring Craft Fair

Which events are currently trending in Chestertown?

The trending searches this month in Chestertown are:

chestertown car show

events happening today near me

chester river chorale celtic christmas

yard sales and estate sale

Which festival events are coming up?

Discover the best festival events happening soon – you don't want to miss them:

Baltimore Taco Festival

THE BLACK MALL SUNDAY - (Bmore's Love Market)

The Masters Ceremony

Thanksgiving In The Tank Room