Festivals in Annapolis, MD.
Craft Shows, Festivals, Vendor Events
Fell's Point Fun Festival
October 2 - 4, 2026
fellspointfest.com
(410) 675-6750
Historic Waterfront at Fell's Point - Baltimore, MD
A festival built by a movement. The Fell's Point Fun Festival began in 1967 as a fundraiser to raise money to fight against a project that would have linked I-83 and I-95 and demolished an extensive area of Fell's Point. Thanks to the initial organizers of this festival our neighborhood fought back and Fell's Point as we know it was saved. Since then, the Annual Fell's Point Fun Festival has grown to cover 6 city blocks in the heart of our beautiful historic, eclectic, and unique neighborhood.
Great Big Fall Home Show
October 10 - 11, 2026
greatbighomeshow.com
(240) 412-8530
Capital Clubhouse - Waldorf, MD
Great Big Home Show | Admission: none | Days/Hours Open: Sat & Sun, 10am‑5pm | Address: 3033 Waldorf Market Place, Waldorf, MD 20603 Don't miss this Great Big Opportunity to save thousands on your next home remodeling project!!!
Savor Bowie Fall Fest
October 10 - 11, 2026
concertsforcausesinc.org
(301) 332-8318
Bowie Towne Center - Bowie, MD
Concerts for Causes Inc. presents Savor Bowie 2025 Food, Wine, and Music festival, now 2 days! featuring Free admission (You heard right, Free Admission) and Complimentary Food and Wine tastings from the top wineries in the area. Vendors and Artisans, Antique and New Car display. Two Stages & many areas of music and other entertainment! Great kid's area! A non-profit organization raising funds to give musical instruments to students.
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Events in Annapolis, MD — upcoming
July 5, 2026
First Sunday Arts Festival - July
Downtown Annapolis, Annapolis, MD
Status: Updated 1/8/2026
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, 2026
First Sunday Arts Festival - August
Downtown Annapolis, Annapolis, MD
Status: Updated 1/8/2026
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, 2026
First Sunday Arts Festival - September
Downtown Annapolis, Annapolis, MD
Status: Updated 1/8/2026
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, 2026
Maryland Seafood Festival
Sandy Point State Park East Beach, Annapolis, MD
Status: Updated 3/18/2026
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 2026 (dates not updated)
Kunta Kinte Heritage Festival
Navy Marine Corps Stadium (Blue Lot), Annapolis, MD
Status: Updated 8/10/2025
This Maryland Festival will have antique/collectibles, commercial/retail, corp./information, crafts, film, fine art, fine craft and homegrown products exhibitors, and 15 food booths. There will be 3 stages with National, Regional and Local talent and the hours will be Sat 10am-7pm.
September 13, 2026
Bay Bridge Paddle
Sandy Point State Park East Beach, Annapolis, MD
Status: Updated 3/18/2026
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.
September 2026 (dates not updated)
Annapolis Fall Home Owners Expo
The Byzantium Conference and Event Center, Annapolis, MD
Status: Updated 9/16/2025
This Maryland Home and Garden Show will have commercial/retail and corp./information exhibitors, and no food booths. There will be 1 stage with National talent and the hours will be Sat 10am-6pm; Sun 12pm-5pm.
September 2026 (dates not updated)
West Annapolis Oktoberfest
Downtown, Annapolis, MD
Status: Updated 8/30/2025
This Maryland Festival will have antique/collectibles, corp./information, crafts, fine art, fine craft and homegrown products exhibitors, and 6 food booths. There will be 1 stage with Regional talent and the hours will be Sun 11am-4pm.
October 4, 2026
First Sunday Arts Festival - October
Downtown Annapolis, Annapolis, MD
Status: Updated 1/8/2026
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 8 - 11, 2026
United States Powerboat Show
Annapolis City Dock & Harbor, Annapolis, MD
Status: Updated 5/5/2026
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, 2026
Annapolis Sailboat Show
Annapolis City Dock & Harbor, Annapolis, MD
Status: Updated 6/10/2026
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, 2026
Art @ the Park
Quiet Waters Park, Annapolis, MD
Status: Updated 1/14/2026
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 2026 (dates not updated)
Fall Festival on the Avenue
Downtown, Annapolis, MD
Status: Updated 9/20/2025
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, 2026
Maryland Renaissance Festival
Crownsville Road, Annapolis, MD
Status: Updated 4/14/2026
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, 2026
First Sunday Arts Festival - November
Downtown Annapolis, Annapolis, MD
Status: Updated 1/8/2026
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, 2026
Annapolis Chocolate Binge Festival
Downtown Annapolis, Annapolis, MD
Status: Updated 1/8/2026
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 2026 (dates not updated)
Annapolis Holiday Market
St. John's College, Annapolis, MD
Status: Updated 12/8/2025
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 4pm-10pm; Fri-Sat 11am-9pm; Sun 11am-5pm.
February 2027 (dates not updated)
Spring Home Owners Expo - Annapolis
The Byzantium Event Center, Annapolis, MD
Status: Updated 9/16/2025
This Maryland Home and Garden Show will have commercial/retail and corp./information exhibitors, and no food booths. Admission tickets are $3 - $5.
April 2027 (dates not updated)
Annapolis Spring Sailboat Show
Annapolis City Dock and Harbor, Annapolis, MD
Status: Updated 3/31/2026
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 2027 (dates not updated)
First Sunday Arts Festival - May
Downtown Annapolis, Annapolis, MD
Status: Updated 1/8/2026
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 2027 (dates not updated)
First Sunday Arts Festival - June
Downtown Annapolis, Annapolis, MD
Status: Updated 1/8/2026
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 2027 (dates not updated)
Arts Annapolis 2026
West St/Calvert St/ Maryland Ave, Annapolis, MD
Status: Updated 4/15/2026
This Maryland Art Show will have fine craft exhibitors and no food booths.
