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Search filters: Events in Annapolis, Maryland.

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Featured Events

April 14, 2024

historic-oakland.com

(410) 730-4801
Historic Oakland Manor - Columbia, MD

Our Annual Wedding & Event Showcase a popular event that highlights local vendors! Join us for an amazing time at Historic Oakland. Vendor Opportunities: Are you a wedding or event professional looking to increase your client base?  Join us for our 24th Wedding Event Showcase. We average 300-500 guests come through our show.

April 20 - 21, 2024

ConcertsforCausesinc.org

(301) 332-8318
Bowie Town Center - Bowie, MD

Complimentary Wine tastings! Great Food Vendors, Exhibitors and Artisans. Many areas of music and other entertainment!

April 27, 2024

tacosntaps.com

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

Put on your party sombrero! This festival will take you South of the Border for some foodie fun. This ALL-YOU-CARE-TO-TASTE Beer & Tequila Festival offers up some of the area's best Tacos and Mexican Food...along with great live music, margaritas, pinata punching, contests and many other surprises. This is NACHO average taco festival.

June 8, 2024

drinkeatrelax.com/event/wine-food-festival-..

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

Same great location as last year! Come and enjoy Wine, Beer, Spirits and Music at the Timonium Fairgrounds. Enjoy a day-drinking garden party filled with lots of green grass, great music and good vibes. The Festival will include International Wine Pavilions, Domestic Wine Tastings, Local Wine Favorites and Great Regional Bands on the Main Stage. Beer and Spirits too! The name says Wine, but the event offers a great selection of beers, with one area dedicated to Local Maryland Beers. As well, you'll see lots of seltzers and canned cocktails. 100+ to sample…in an ALL-YOU-CARE-TO-TASTE format with your Souvenir cup. Great Food Trucks!

June 8, 2024

facebook.com/events/928837721776370/?aconte..

(410) 417-6668
Harford County Equestrian Center - Bel Air, MD

Come alone or join a friend at our Annual Tastes & Tunes Festival on Saturday, June 8th, 11A-8:30P at the beautifully scenic grounds of the Harford County Equestrian Center (Bel Air, MD). Will YOU be there? 𝐎𝐍𝐋𝐘 𝟒𝟎 𝐦𝐢𝐥𝐞𝐬 outside of ᗷᗩᒪTIᗰOᖇE. Come spend the day on the picturesque grounds of the Harford County Equestrian Center listening to RNB, Smooth Jazz & Neo Soul, dancing, and great tasty treats--food & beverage.

June 8 - 9, 2024

gem-show.com

(301) 807-9745
Howard County Fairgrounds - West Friendship, MD

The Gem Miner's Jubilee Spring Show is an annual exhibition and sale of some of the finest products & collectibles available to collectors of Earth's treasures. 60+ vendors from around the country converge at the Howard County Fairgrounds in West Friendship MD for a festival of gems, minerals, fossils, beads, and jewelry. This is an opportunity to meet source dealers bringing the finest natural treasures at discounted prices. There is a separate Wholesale area to the trade. Free parking and an air-conditioned hall.

October 5, 2024

dasbestoktoberfest.com

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

Over 150 Beers, wines and Schnapps highlight this all-you-care-to-taste German-themed extravaganza! Join in the Beer Games with your friends, dance with the live music and kick it up with the oompah bands!

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.

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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

There will be 1 stage with International talent. The entertainment will be Variety.
  • # of Exhibitors: 65
  • Juried: no
  • Prize Money: na
April 26 - 28, 2024

Annapolis Spring Sailboat Show

Annapolis City Dock and Harbor, Annapolis, MD

Status: Updated 2/1/2024

  • # of Exhibitors: 175
  • Juried: no
  • Prize Money: na
Annapolis Up Rigging Festival
May 2024 (dates not updated)

Annapolis Up Rigging Festival

City Dock in Downtown Annapolis, Annapolis, MD

Status: Updated 12/3/2022

There will be 1 stage with Local talent. The entertainment will be Variety, and there will be other activities like tall ships and demonstrations.
  • # of Exhibitors: 50
  • Juried: no
  • Prize Money: na
May 5, 2024

First Sunday Arts Festival - May

Downtown Annapolis, Annapolis, MD

Status: Updated 2/12/2024

There will be 2 stages with Local talent. The entertainment will be Classical/Symphony, Country, Gospel and Rock.
  • # of Exhibitors: 130
  • Juried: no
  • Prize Money: na
June 2, 2024

First Sunday Arts Festival - June

Downtown Annapolis, Annapolis, MD

Status: Updated 1/15/2024

There will be 3 stages with Local talent. The entertainment will be Classical/Symphony, Country, Gospel and Rock, and there will be other activities like demonstrations.
  • # of Exhibitors: 130
  • Juried: no
  • Prize Money: na
July 7, 2024

First Sunday Arts Festival - July

Downtown Annapolis, Annapolis, MD

Status: Updated 2/13/2024

There will be 3 stages with Local talent. The entertainment will be Classical/Symphony, Country, Gospel and Rock, and there will be other activities like demonstrations.
  • # of Exhibitors: 130
  • Juried: no
  • Prize Money: na
August 4, 2024

First Sunday Arts Festival - August

Downtown Annapolis, Annapolis, MD

Status: Updated 2/13/2024

There will be 3 stages with Local talent. The entertainment will be Classical/Symphony, Country, Gospel, Rock and Variety, and there will be other activities like demonstrations.
  • # of Exhibitors: 130
  • Juried: no
  • Prize Money: na
August 24 - October 20, 2024

Maryland Renaissance Festival

Crownsville Road, Annapolis, MD

Status: Updated 2/8/2024

There will be 10 stages with International, National and Regional talent. The entertainment will be Folk and Variety, and there will be other activities like children's area, games.
  • # of Exhibitors: 118
  • Juried: yes
  • Prize Money: na
September 1, 2024

First Sunday Arts Festival - September

Downtown Annapolis, Annapolis, MD

Status: Updated 2/13/2024

There will be 3 stages with Local talent. The entertainment will be Variety, and there will be other activities like demonstrations.
  • # of Exhibitors: 130
  • Juried: no
  • Prize Money: na
September 14 - 15, 2024

Maryland Seafood Festival

Sandy Point State Park East Beach, Annapolis, MD

Status: Updated 12/13/2023

There will be 1 stage with Regional and Local talent. The entertainment will be Beach, Bluegrass, Blues, Cajun/Zydeco, Country, Jazz, Reggae, Rock, Top Forty/Pop and Variety, and there will be other activities like crab picking contest, kids area.
  • # of Exhibitors: 50
  • Juried: no
  • Prize Money: na
September 15, 2024

Bay Bridge Paddle

Sandy Point State Park East Beach, Annapolis, MD

Status: Updated 12/13/2023

There will be 1 stage with Local talent. The entertainment will be Beach and Reggae.
  • # of Exhibitors: 5
  • Juried: no
  • Prize Money: na
Kunta Kinte Heritage Festival
September 2024 (dates not updated)

Kunta Kinte Heritage Festival

Annapolis City Dock - Susan Campbell Park, Annapolis, MD

Status: Updated 9/14/2023

There will be 3 stages with National, Regional and Local talent. The entertainment will be Blues, Children's, Christian, Ethnic, Funk, Gospel, Jazz, Latin, Rap/Hip-hop, R & B/Soul, Reggae, Roots, Spoken Word and World, and there will be other activities like children's tent and education booths.
  • # of Exhibitors: 70
  • Juried: no
  • Prize Money: na
West Annapolis Oktoberfest
September 2024 (dates not updated)

West Annapolis Oktoberfest

Downtown, Annapolis, MD

Status: Updated 9/15/2023

There will be 1 stage with Regional talent. The entertainment will be Ethnic.
  • # of Exhibitors: 110
  • Juried: no
  • Prize Money: na
Annapolis Fall Home Owners Expo
September - October 2024 (dates not updated)

Annapolis Fall Home Owners Expo

The Byzantium Conference and Event Center, Annapolis, MD

Status: Updated 7/3/2023

There will be 1 stage with National talent. The entertainment will be Variety.
  • # of Exhibitors: tba
  • Juried:
  • Prize Money: na
United States Powerboat Show
October 2024 (dates not updated)

United States Powerboat Show

Annapolis City Dock & Harbor, Annapolis, MD

Status: Updated 8/14/2023

  • # of Exhibitors: 400
  • Juried: no
  • Prize Money: na
October 6, 2024

First Sunday Arts Festival - October

Downtown Annapolis, Annapolis, MD

Status: Updated 2/13/2024

There will be 3 stages with Local talent. The entertainment will be Variety, and there will be other activities like demonstrations.
  • # of Exhibitors: 130
  • Juried: no
  • Prize Money: na
October 10 - 14, 2024

United States Sailboat Show

Annapolis City Dock & Harbor, Annapolis, MD

Status: Updated 1/17/2024

  • # of Exhibitors: 700
  • Juried: no
  • Prize Money: na
Art @ the Park
October 2024 (dates not updated)

Art @ the Park

Quiet Waters Park, Annapolis, MD

Status: Updated 9/29/2023

There will be 1 stage with Regional talent. The entertainment will be Bluegrass, Blues, Cajun/Zydeco, Country, Folk, Jazz, R & B/Soul, Reggae and Rock, and there will be other activities like demostrations.
  • # of Exhibitors: 70+
  • Juried: yes
  • Prize Money: na
October 19, 2024

Mid Atlantic Health Expo

Double Tree by Hilton, Annapolis, MD

Status: Updated 1/22/2024

  • # of Exhibitors: 50
  • Juried: no
  • Prize Money: na
Fall Festival on the Avenue
October 2024 (dates not updated)

Fall Festival on the Avenue

Downtown, Annapolis, MD

Status: Updated 1/9/2023

  • # of Exhibitors: 50
  • Juried: no
  • Prize Money: na
Harvest Hootenanny
October 2024 (dates not updated)

Harvest Hootenanny

Chesapeake Children's Museum, Annapolis, MD

Status: Updated 10/5/2023

There will be 1 stage with Local talent. The entertainment will be Americana, Bluegrass, Country and Folk, and there will be other activities like petting zoo of farm animals, pumpkin painting, scarecrow stuffing, mini-hayrides.
  • # of Exhibitors: 20
  • Juried: no
  • Prize Money: na
November 3, 2024

First Sunday Arts Festival - November

Downtown Annapolis, Annapolis, MD

Status: Updated 2/13/2024

There will be 4 stages with Local talent. The entertainment will be Variety, and there will be other activities like demonstrations.
  • # of Exhibitors: 130
  • Juried: no
  • Prize Money: na
December 1, 2024

Annapolis Chocolate Binge Festival

Downtown Annapolis, Annapolis, MD

Status: Updated 2/13/2024

There will be 2 stages with Local talent. The entertainment will be Variety, and there will be other activities like demonstrations.
  • # of Exhibitors: 60
  • Juried: no
  • Prize Money: na
Tis the Season
December 2024 (dates not updated)

Tis the Season

Annapolis Mall, Annapolis, MD

Status: Updated 5/14/2023

There will be 1 stage with Local talent. The entertainment will be Variety.
  • # of Exhibitors: 40
  • Juried: no
  • Prize Money: na