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Festivals in Annapolis, MD.
Craft Shows, Festivals

Featured Events

October 19, 2024

whiskeywinefire.com

(800) 830-3976
Maryland State Fairgrounds - Timonium, MD

An elegant evening in the Infield - this is an exclusive foodie celebration that features: Whiskey Bars, Elegant Wines and cocktails, great music, tented Food Stations, Food Trucks and restaurants, and Bonfires throughout. Relax around the fire gardens and enjoy an inspired take on fire-kissed BBQ, specialty grilling, and drink pairings. Enjoy the firebreathers and artists who set the night ablaze. Please dress appropriately, the event is outdoors. Souvenir glass to taste Whiskeys and wines and Food Galore! Enjoy great BBQ, grilled meat selections, and other goodies...Food Trucks, plus a S'mores station

October 26, 2024

wesleychapelurbana.com

(301) 662-5769
Urbana Vol. Fire & Rescue Company - Frederick, MD

Vendors will sell original crafts including jewelry, stained glass, woodworking, skin care, primitives, knitted and crochet, candles, fabric & textiles, floral, pottery, and seasonal crafts, artwork in several mediums and photography. Breakfast, lunch and bake table provided by the Church ladies of Wesley Chapel.

December 12 - 30, 2024

mdholidaylights.com

(800) 830-3976
Maryland State Fairgrounds - Infield - Timonium, MD - Timonium, MD

Capture the Magic...Create a New Holiday Tradition at the new outdoor Maryland Holiday Light Spectacular - see over a million beautiful lights and dozens of displays on a half-mile walking trail. See larger than life holiday scenes, wonderful music throughout and oversized snow globes. There will be magical interactive wand elements throughout the event, Children's Activities, a Moon Bounce a Holiday Village complete with Boutiques, Shops and Rotating Food Trucks and so much more!

December 13 - 15, 2024

(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.

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Events in Annapolis, MD — upcoming

October 10 - 14, 2024

United States Sailboat Show

Annapolis City Dock & Harbor, Annapolis, MD

Status: Updated 1/17/2024

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.
August 24 - October 20, 2024

Maryland Renaissance Festival

Crownsville Road, Annapolis, MD

Status: Updated 2/8/2024

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 2024 (dates not updated)

Fall Festival on the Avenue

Downtown, Annapolis, MD

Status: Updated 1/9/2023

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.
Harvest Hootenanny
October 2024 (dates not updated)

Harvest Hootenanny

Chesapeake Children's Museum, Annapolis, MD

Status: Updated 10/5/2023

A Family & Kids Festival organized by Chesapeake Childrens' Museum.
This Maryland Family & Kids Festival will have crafts, flea market and homegrown products exhibitors, and 4 food booths. There will be 1 stage with Local talent and the hours will be Sun 10am-1pm. Admission tickets are $8. This event will also include: petting zoo of farm animals, pumpkin painting, scarecrow stuffing, mini-hayrides.
November 3, 2024

First Sunday Arts Festival - November

Downtown Annapolis, Annapolis, MD

Status: Updated 2/13/2024

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 4 stages with Local talent and the hours will be Sun 11am-5pm. This event will also include demonstrations.
December 1, 2024

Annapolis Chocolate Binge Festival

Downtown Annapolis, Annapolis, MD

Status: Updated 2/13/2024

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 12 - 15, 2024

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 11am-9pm, Sat 11am-9pm, Sun 11am-5pm.
Annapolis Spring Home Owners Expo
February 2025 (dates not updated)

Annapolis Spring Home Owners Expo

The Byzantium Event Center, Annapolis, MD

Status: Updated 10/23/2023

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 International talent and the hours will be Sat 10am-6pm, Sun 12pm-5pm. Admission tickets are $3 - $5.
Annapolis Spring Sailboat Show
April 2025 (dates not updated)

Annapolis Spring Sailboat Show

Annapolis City Dock and Harbor, Annapolis, MD

Status: Updated 2/1/2024

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 2025 (dates not updated)

First Sunday Arts Festival - May

Downtown Annapolis, Annapolis, MD

Status: Updated 2/12/2024

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 2025 (dates not updated)

First Sunday Arts Festival - June

Downtown Annapolis, Annapolis, MD

Status: Updated 1/15/2024

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 2025 (dates not updated)

First Sunday Arts Festival - July

Downtown Annapolis, Annapolis, MD

Status: Updated 2/13/2024

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 2025 (dates not updated)

First Sunday Arts Festival - August

Downtown Annapolis, Annapolis, MD

Status: Updated 2/13/2024

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 2025 (dates not updated)

First Sunday Arts Festival - September

Downtown Annapolis, Annapolis, MD

Status: Updated 2/13/2024

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 2025 (dates not updated)

Kunta Kinte Heritage Festival

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

Status: Updated 8/6/2024

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. This event will also include children's tent and education booths.
Maryland Seafood Festival
September 2025 (dates not updated)

Maryland Seafood Festival

Sandy Point State Park East Beach, Annapolis, MD

Status: Updated 12/13/2023

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-7pm. Admission tickets are $15 - $100. This event will also include: crab picking contest, kids area.
Bay Bridge Paddle
September 2025 (dates not updated)

Bay Bridge Paddle

Sandy Point State Park East Beach, Annapolis, MD

Status: Updated 12/13/2023

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.
West Annapolis Oktoberfest
September 2025 (dates not updated)

West Annapolis Oktoberfest

Downtown, Annapolis, MD

Status: Updated 8/7/2024

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.
Annapolis Fall Home Owners Expo
September 2025 (dates not updated)

Annapolis Fall Home Owners Expo

The Byzantium Conference and Event Center, Annapolis, MD

Status: Updated 8/5/2024

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. Admission tickets are $3 - $5.
United States Powerboat Show
October 2025 (dates not updated)

United States Powerboat Show

Annapolis City Dock & Harbor, Annapolis, MD

Status: Updated 6/25/2024

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 2025 (dates not updated)

First Sunday Arts Festival - October

Downtown Annapolis, Annapolis, MD

Status: Updated 2/13/2024

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.
Art @ the Park
October 2025 (dates not updated)

Art @ the Park

Quiet Waters Park, Annapolis, MD

Status: Updated 4/19/2024

A Music Festival organized by Friends of Quiet Waters Park Annapolis MD.
This Maryland Music Festival will have fine art and fine craft exhibitors, and 4 food booths. There will be 1 stage with Regional talent and the hours will be Sat 10am-5pm, Sun 10am-4pm. Admission tickets are $1 - $6. This event will also include demostrations.