Art shows and craft fairs 2026–2027Maryland Cities and TownsAnnapolis, Baltimore, Bethesda, Boonsboro, Bowie, Boyds, Calverton, Cascade, Cockeysville, College Park, Columbia, Crownsville, Dowell, Easton, Elkton, Ellicott City, Fallston, Finksburg, Frederick, Gaithersburg, Glen Burnie, Grasonville, Greenbelt, Havre de Grace, Huntingtown, Md, Laurel, Leitersburg, Leonardtown, Lutherville-Timonium, Middle River, Myersville, Nottingham, Ocean City, Oxon Hill, Pocomoke City, Poolesville, Prince Frederick, Reisterstown, Rockville, Saint Michaels, Salisbury, Silver Spring, Solomons, Taneytown, Timonium, Towson, Waldorf, West Friendship, WestminsterAttend Your Favorite Art Shows and Art Fairs of the Year in Annapolis, MD
April 24 - 26, 2026Annapolis Spring Sailboat ShowAnnapolis City Dock and Harbor, Annapolis, MD Status: Updated 3/31/2026
A Boat Auto Camping Show organized by Annapolis Boat Shows.
This Maryland Boat Auto Camping Show will have commercial/retail and corp./information exhibitors, and no food booths. Admission tickets are $20. This event will also include demonstrations.
May 3, 2026First Sunday Arts Festival - MayDowntown Annapolis, Annapolis, MD Status: Updated 1/8/2026
A Festival organized by Inner West Street Association.
This Maryland Festival 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.
June 7, 2026First Sunday Arts Festival - JuneDowntown Annapolis, Annapolis, MD Status: Updated 1/8/2026
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.
June 13, 2026Arts Annapolis 2026Historic Annapolis - various, Annapolis, MD Status: Updated 3/18/2026
A Music Festival organized by Inner West Street Association.
This Maryland Music Festival will have fine art exhibitors and no food booths. There will be 4 stages with Regional and Local talent and the hours will be Sat 12pm-10pm.
July 5, 2026First Sunday Arts Festival - JulyDowntown Annapolis, Annapolis, MD Status: Updated 1/8/2026
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 2, 2026First Sunday Arts Festival - AugustDowntown Annapolis, Annapolis, MD Status: Updated 1/8/2026
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 6, 2026First Sunday Arts Festival - SeptemberDowntown Annapolis, Annapolis, MD Status: Updated 1/8/2026
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 12 - 13, 2026Maryland Seafood FestivalSandy Point State Park East Beach, Annapolis, MD Status: Updated 3/18/2026
A Food Festival organized by Peake Events Inc..
This Maryland Food Festival will have commercial/retail, crafts, fine art and fine craft exhibitors, and 18 food booths. There will be 1 stage with Regional and Local talent and the hours will be Sat 11am-7pm; Sun 11am-6pm. Admission tickets are $17 - $200.
September 13, 2026Bay Bridge PaddleSandy Point State Park East Beach, Annapolis, MD Status: Updated 3/18/2026
A Sports Event organized by Peake Events Inc..
This Maryland Sports Event will have commercial/retail exhibitors and 5 food booths. There will be 1 stage with Local talent and the hours will be Sun 7am-2pm. Admission tickets are $45 - $110.
October 4, 2026First Sunday Arts Festival - OctoberDowntown Annapolis, Annapolis, MD Status: Updated 1/8/2026
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 17 - 18, 2026Art @ the ParkQuiet Waters Park, Annapolis, MD Status: Updated 1/14/2026
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-Sun 10am-4pm. This event will also include demostrations.
November 1, 2026First Sunday Arts Festival - NovemberDowntown Annapolis, Annapolis, MD Status: Updated 1/8/2026
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 6, 2026Annapolis Chocolate Binge FestivalDowntown Annapolis, Annapolis, MD Status: Updated 1/8/2026
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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