Art shows and craft fairs 2026–2027Maryland Cities and TownsAnnapolis, Baltimore, Boonsboro, Bowie, Boyds, Calverton, Cascade, College Park, Cooksville, Deale, Dowell, Easton, Ellicott City, Frederick, Gaithersburg, Germantown, Glen Burnie, Greenbelt, Laplata, Laurel, Leonardtown, Linthicum, Lutherville, Lutherville-Timonium, Mchenry, Myersville, Ocean City, Oxon Hill, Parkville, Pikesville, Pocomoke City, Reisterstown, Salisbury, Shady Side, Silver Spring, Thurmont, Tilghman, Timonium, Waldorf, West Friendship, WestminsterAttend Your Favorite Art Shows and Art Fairs of the Year in Annapolis, MD
October 8 - 11, 2026United States Powerboat ShowAnnapolis City Dock & Harbor, Annapolis, MD Status: Updated 5/5/2026
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 $5 - $48.
October 15 - 18, 2026Annapolis Sailboat ShowAnnapolis City Dock & Harbor, Annapolis, MD Status: Updated 6/10/2026
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 $5 - $48.
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.
October 18, 2026Fall Festival on the AvenueDowntown, Annapolis, MD Status: Updated 10/4/2026
A Holiday Celebration organized by Maryland Ave & State Circle Assocation.
This Maryland Holiday Celebration will have antique/collectibles, crafts, fine art, fine craft and homegrown products exhibitors, and 6 food booths.
August 29 - October 25, 2026Maryland Renaissance FestivalCrownsville Road, Annapolis, MD Status: Updated 4/14/2026
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 . Admission tickets are $8 - $30. This event will also include: children's area, games.
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 7/26/2026
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.
December 4 - 13, 2026Annapolis Holiday MarketAnnapolis Mall, Annapolis, MD Status: Updated 9/8/2026
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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