Festivals in Annapolis, MD.
Craft Shows, Festivals, Holiday Celebrations
World of Pets Expo - Timonium
January 29 - 31, 2027
worldofpets.org
(800) 882-9894
Maryland State Fairgrounds - Timonium, MD
The World of Pets Expo is a fun and educational experience for the entire family and pets of all kind. For less than the price of a movie ticket you and your family can experience a full day of education and entertainment. There is truly something for every animal lover and pet owner. The World of Pets Expo will feature many returning popular entertainers and many new and exciting acts and exhibitors. In addition, there are educational opportunities, workshops and seminars addressing unique pet needs, food and nutrition, behavior and more, all offered by pet and animal experts.
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Events in Annapolis, MD — upcoming
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 7/26/2026
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 4 - 13, 2026
Annapolis Holiday Market
Annapolis Mall, Annapolis, MD
Status: Updated 9/8/2026
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.
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.
July 2027 (dates not updated)
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 2027 (dates not updated)
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 2027 (dates not updated)
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 2027 (dates not updated)
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 2027 (dates not updated)
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 2027 (dates not updated)
Kunta Kinte Heritage Festival
Navy Marine Corps Stadium (Blue Lot), Annapolis, MD
Status: Updated 8/27/2026
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 2027 (dates not updated)
Annapolis Fall Home Owners Expo
The Byzantium Conference and Event Center, Annapolis, MD
Status: Updated 8/30/2026
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 11:30am-4:30pm.
September 2027 (dates not updated)
West Annapolis Oktoberfest
Downtown, Annapolis, MD
Status: Updated 8/16/2026
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 2027 (dates not updated)
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 2027 (dates not updated)
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 2027 (dates not updated)
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 2027 (dates not updated)
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 2027 (dates not updated)
Fall Festival on the Avenue
Downtown, Annapolis, MD
Status: Updated 10/4/2026
This Maryland Holiday Celebration will have antique/collectibles, crafts, fine art, fine craft and homegrown products exhibitors, and 6 food booths.
August - October 2027 (dates not updated)
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.
