Music Festivals 2025–2026Maryland Cities and TownsAnnapolis, Baltimore, Bel Air, Boonsboro, Bowie, Cockeysville, Columbia, Crisfield, Crownsville, Darlington, Deale, Easton, Elkton, Essex, Finksburg, Frederick, Gaithersburg, Greenbelt, Havre de Grace, Hyattsville, La Plata, Lanham, Laurel, Leitersburg, Leonardtown, Lutherville-Timonium, Mchenry, Ocean City, Pittsville, Pocomoke City, Prince Frederick, Rising Sun, Silver Spring, Solomons, Taneytown, Thurmont, Timonium, West Friendship, WestminsterAttend Your Favorite Music Festivals in Annapolis, MD![]() July 6, 2025First Sunday Arts Festival - JulyDowntown Annapolis, Annapolis, MD Status: Updated 1/23/2025
A Craft Show organized by Inner West Street Association.
This Maryland Craft Show will have antique/collectibles, crafts, fine art and fine craft exhibitors, and 8 food booths. There will be 3 stages with Local talent and the hours will be Sun 11am-5pm. This event will also include demonstrations. ![]() August 3, 2025First Sunday Arts Festival - AugustDowntown Annapolis, Annapolis, MD Status: Updated 1/23/2025
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 3 stages with Local talent and the hours will be Sun 11am-5pm. This event will also include demonstrations. ![]() September 7, 2025First Sunday Arts Festival - SeptemberDowntown Annapolis, Annapolis, MD Status: Updated 1/23/2025
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 3 stages with Local talent and the hours will be Sun 11am-5pm. This event will also include demonstrations. ![]() October 5, 2025First Sunday Arts Festival - OctoberDowntown Annapolis, Annapolis, MD Status: Updated 1/23/2025
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 3 stages with Local talent and the hours will be Sun 11am-5pm. This event will also include demonstrations. ![]() October 11 - 12, 2025Art @ the ParkQuiet Waters Park, Annapolis, MD Status: Updated 5/13/2025
A Music Festival organized by Quiet Waters Park.
This Maryland Music Festival will have crafts, fine art and fine craft exhibitors, and 4 food booths. There will be 1 stage with Regional talent and the hours will be Sat 10am-4pm, Sun 10am-4pm. This event will also include demostrations. ![]() August 23 - October 19, 2025Maryland Renaissance FestivalCrownsville Road, Annapolis, MD Status: Updated 2/21/2025
A Renaissance-Medieval-Pirate Fair organized by Maryland Renaissance Festival, Ltd..
This Maryland Renaissance-Medieval-Pirate Fair will have crafts, fine art and fine craft exhibitors, and 42 food booths. There will be 10 stages with International, National and Regional talent and the hours will be Sat 10am-7pm, Sun 10am-7pm, Mon closed, Tue closed, Wed closed, Thu closed, Fri closed, Sat 10am-7pm, Sun 10am-7pm, Mon 10am-7pm, Tue closed, Wed closed, Thu closed, Fri closed, Sat 10am-7pm, Sun 10am-7pm, Mon closed, Tue closed, Wed closed, Thu closed, Fri closed, Sat 10am-7pm, Sun 10am-7pm, Mon closed, Tue closed, Wed closed, Thu closed, Fri closed, Sat 10am-7pm, Sun 10am-7pm, Mon 10am-7pm. Admission tickets are $8 - $30. This event will also include: children's area, games. ![]() November 2, 2025First Sunday Arts Festival - NovemberDowntown Annapolis, Annapolis, MD Status: Updated 1/23/2025
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. ![]() December 7, 2025Annapolis Chocolate Binge FestivalDowntown Annapolis, Annapolis, MD Status: Updated 1/23/2025
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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