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Festivals in Annapolis, MD.
Craft Shows, Festivals, Holiday Celebrations

Featured Events

December 6, 2025

vendormembersgroup.com

Timonium UMC - Timonium, MD

Vendor Members Group cordially invites you to the 2025 Holiday Market of CRAFTS GALORE! Sleigh bells will ring and jingle for this ultimate Holiday Shopping experience. Before heading over to Grandma's house, fill your sleigh ride w/an assortment of unique, affordable artwork (wooden, paper, acrylic, textile, etc), home decor, seasonal & custom designed wearables, jewelry, personal adornments, self-care essentials, polished stones, scented candles, specialty baked goods — All made by talented small business owners and food preparers Plus, you can have your event purchases wrapped while capturing a keepsake photo with Santa! See you there!

December 12 - 14, 2025

(301) 643-9158
Charles County Fair Grounds - Laplata, MD

Christmas market with 175 crafters. We light up the fairgrounds with thousands of lights. Santa comes to town on a fire truck. There is a live nativity, Live Entertainment a kid's area, and Fireworks on Saturday. All spaces for Bakers, Candy makers, and Soap makers inside are full.

January 23 - 25, 2026

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.

April 4, 2026

Official Website

Timonium UMC - Timonium, MD

Independently operated by Vendor Members Group, the market of CRAFTS GALORE! is a juried craft and artisan show held multiple times throughout the year. In 2026, held the first Saturday of April, May, (tentatively) June, Sep, Oct, Nov, and Dec from 9:30 am-2:30 pm. Meet us there!

May 2, 2026

Official Website

Timonium UMC - Timonium, MD

Independently operated by Vendor Members Group, the market of CRAFTS GALORE! is a juried craft and artisan show held multiple times throughout the year. In 2026, held the first Saturday of April, May, (tentatively) June, Sep, Oct, Nov, and Dec from 9:30 am-2:30 pm. Meet us there!

June 6, 2026

Official Website

Timonium UMC - Timonium, MD

Independently operated by Vendor Members Group, the market of CRAFTS GALORE! is a juried craft and artisan show held multiple times throughout the year. In 2026, held the first Saturday of April, May, (tentatively) June, Sep, Oct, Nov, and Dec from 9:30 am-2:30 pm. Meet us there!

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Events in Annapolis, MD — upcoming

December 7, 2025

Annapolis Chocolate Binge Festival

Downtown Annapolis, Annapolis, MD

Status: Updated 7/16/2025

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.
Annapolis Holiday Market
December 2025 (dates not updated)

Annapolis Holiday Market

City Dock, Annapolis, MD

Status: Updated 10/11/2024

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 4pm-10pm; Fri-Sat 11am-9pm; Sun 11am-5pm.
February 21 - 22, 2026

Spring Home Owners Expo - Annapolis

The Byzantium Event Center, Annapolis, MD

Status: Updated 9/16/2025

A Home and Garden Show organized by Mid Atlantic Expositions and Entertainment.
This Maryland Home and Garden Show will have commercial/retail and corp./information exhibitors, and no food booths. Admission tickets are $3 - $5.
Annapolis Spring Sailboat Show
April 2026 (dates not updated)

Annapolis Spring Sailboat Show

Annapolis City Dock and Harbor, Annapolis, MD

Status: Updated 12/10/2024

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 $18 - $20. This event will also include demonstrations.
First Sunday Arts Festival - May
May 2026 (dates not updated)

First Sunday Arts Festival - May

Downtown 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 8 food booths. There will be 2 stages with Local talent and the hours will be Sun 11am-5pm.
First Sunday Arts Festival - June
June 2026 (dates not updated)

First Sunday Arts Festival - June

Downtown 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.
First Sunday Arts Festival - July
July 2026 (dates not updated)

First Sunday Arts Festival - July

Downtown 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.
First Sunday Arts Festival - August
August 2026 (dates not updated)

First Sunday Arts Festival - August

Downtown 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.
First Sunday Arts Festival - September
September 2026 (dates not updated)

First Sunday Arts Festival - September

Downtown 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.
Kunta Kinte Heritage Festival
September 2026 (dates not updated)

Kunta Kinte Heritage Festival

Navy Marine Corps Stadium (Blue Lot), Annapolis, MD

Status: Updated 8/10/2025

A Festival organized by Kunta Kinte Celebrations, Inc..
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.
Maryland Seafood Festival
September 2026 (dates not updated)

Maryland Seafood Festival

Sandy Point State Park East Beach, Annapolis, MD

Status: Updated 8/11/2025

A Food Festival organized by ABC 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.
Bay Bridge Paddle
September 2026 (dates not updated)

Bay Bridge Paddle

Sandy Point State Park East Beach, Annapolis, MD

Status: Updated 8/12/2025

A Sports Event organized by ABC 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.
Annapolis Fall Home Owners Expo
September 2026 (dates not updated)

Annapolis Fall Home Owners Expo

The Byzantium Conference and Event Center, Annapolis, MD

Status: Updated 9/16/2025

A Home and Garden Show organized by Mid Atlantic Expositions and Entertainment.
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.
West Annapolis Oktoberfest
September 2026 (dates not updated)

West Annapolis Oktoberfest

Downtown, Annapolis, MD

Status: Updated 8/30/2025

A Festival organized by West Annapolis Business Affiliation, Inc.
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.
United States Powerboat Show
October 2026 (dates not updated)

United States Powerboat Show

Annapolis City Dock & Harbor, Annapolis, MD

Status: Updated 12/10/2024

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.
First Sunday Arts Festival - October
October 2026 (dates not updated)

First Sunday Arts Festival - October

Downtown 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.
Annapolis Sailboat Show
October 2026 (dates not updated)

Annapolis Sailboat Show

Annapolis City Dock & Harbor, Annapolis, MD

Status: Updated 12/10/2024

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.
Art @ the Park
October 2026 (dates not updated)

Art @ the Park

Quiet 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-Sun 10am-4pm. This event will also include demostrations.
Maryland Renaissance Festival
August - October 2026 (dates not updated)

Maryland Renaissance Festival

Crownsville 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.
Fall Festival on the Avenue
October 2026 (dates not updated)

Fall Festival on the Avenue

Downtown, Annapolis, MD

Status: Updated 9/20/2025

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.
First Sunday Arts Festival - November
November 2026 (dates not updated)

First Sunday Arts Festival - November

Downtown 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.