Maryland Fairs, Festivals & Art Shows
Music Festivals 2026–2027
Cities / Towns
Annapolis Baltimore Boonsboro Brunswick Calverton Deale Dowell Easton Gaithersburg Germantown Greenbelt Laplata Laurel Lutherville-Timonium Ocean City Oxon Hill Pikesville Pocomoke City Rockville Silver Spring Timonium West Friendship

Music Festivals 2026–2027

Maryland Cities and Towns

Annapolis, Baltimore, Boonsboro, Brunswick, Calverton, Deale, Dowell, Easton, Gaithersburg, Germantown, Greenbelt, Laplata, Laurel, Lutherville-Timonium, Ocean City, Oxon Hill, Pikesville, Pocomoke City, Rockville, Silver Spring, Timonium, West Friendship

Attend Your Favorite Music Festivals in Annapolis, MD

 
First Sunday Arts Festival - November
November 1, 2026

First Sunday Arts Festival - November

Downtown Annapolis, Annapolis, MD

Status: Updated 1/8/2026

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A Craft Show organized by Inner West Street Association.
This Maryland Craft Show will have crafts, fine art and fine craft exhibitors, and 8 food booths. There will be 2 stages with Local talent and the hours will be Sun 11am-5pm. This event will also include demonstrations.
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Annapolis Chocolate Binge Festival
December 6, 2026

Annapolis Chocolate Binge Festival

Downtown Annapolis, Annapolis, MD

Status: Updated 7/26/2026

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A Festival organized by Inner West Street Association.
This Maryland Festival will have crafts, fine art and fine craft exhibitors, and no food booths. There will be 2 stages with Local talent and the hours will be Sun 11am-4pm. This event will also include demonstrations.
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Annapolis Holiday Market
December 4 - 13, 2026

Annapolis Holiday Market

Annapolis Mall, Annapolis, MD

Status: Updated 9/8/2026

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A Craft Show organized by Evans Management.
This Maryland Craft Show will have crafts, fine art and fine craft exhibitors, and 6 food booths. There will be 1 stage with Local talent and the hours will be Thu-Sat 11am-9pm; Sun 11am-7pm; Mon-Wed closed.
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