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Maryland >  Maryland: May Festivals

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Maryland:  January/February/March   -   April   -   MAY   -   June/July  -  August   -   September   -   October   -   November/December

Check previous year if event is not yet updated to current year

2024 MARYLAND - MAY 2024
Food & Wine Festivals, Shows & Local Events

(see also: 2022  -  2020  -  2019  -  2016  -  2015)


May 3, 2024
School Lunch Hero Day
A chance to showcase the difference school nutrition professionals make for every child who comes through the cafeteria.

May 4, 2024
Annual Sykesville Art and Wine Festival - Sykesville, Maryland
Juried Artists showcasing and selling everything from paintings, photography, pottery, fabric, jewerly, sculptures and more. Live Music, Maryland Wineries and Food.

May 4-5, 2024 - 51st Annual Maryland Sheep & Wool Festival
West Friendship, Maryland
The Maryland Sheep & Wool Festival is one of the largest festivals of its kind celebrating all things sheep, from hoof to handwoven.

May 11, 2024  Maryland Craft Beer Festival - Frederick, Maryland
Up to 40+ Maryland breweries will be present with over 200 different beers. The event includes on-site brewing demonstrations, rare bottles and kegs, one of a kind casks and VIP craft beer gifts that will blow your mind! This family-friendly festival features live music, fresh foods, kid's activities, and local exhibitors.

May 12, 2024 - MOTHERS' DAY - Nationwide
Most restaurants in the U.S. have special events scheduled for today. They are too numerous to list. (2nd Sun).

May 25-26, 2024  Brew at the Zoo - Baltimore, Maryland
Bears, beers & bands!  Brew at the Zoo tickets will include: Admission to The Zoo, Admission into the event area, unlimited beer & wine sampling, a commemorative tasting glass, live music, KidZone, and access to food & artisan vendors. Famous Dave’s BBQ VIP tickets will be available and will sell out.


May 25-26, 2024  Caribbean Festival  - Mt. Airy, Maryland
The Caribbean Festival is a one of a kind festival that brings together the most authentic and lively expressions of Caribbean life. The event features music, food and arts from across the region. With a full day of live entertainment each day, this two-day festival is sure to be an experience you’ll never forget!

May 26, 2024  Annual Soft Shell Festival - Crisfield, Maryland
Noon-4 pm. Seafood/sides/beverage. Kids' activities, arts and crafts, demonstrations, Watermen's Hall of Fame, fresh crab cakes & soft crabs.

2020 MARYLAND - MAY 2020
Food & Wine Festivals, Shows & Local Events
events waiting for new dates

May 5, 2020  Highlandtown Wine Festival - Baltimore, Maryland
EVENT POSTPONED UNTIL THE FALL OF 2020 DUE TO CORONAVIRUS.  A celebration of homemade wine, gourmet food and music at the 16th Annual Highlandtown Wine Festival. Homemade Wine Competition, Wine Tastings, Children's Activities, Arts & Crafts Vendors, Food, and Music.  Attendance: 1,000.

May 16, 2020  Strawberry Festival - Marion Station, Maryland

May 30, 2020  Wine & Food Festival - Hunt Valley, Maryland
Over 100 Different INTERNATIONAL and LOCAL Wines, Beers, and Spirits. The title says wine but there are all types of adult beverages offered, sampled, and compared.  A souvenir glass to take home.  Great food to taste and to buy from some of the area's hottest restaurants and great food trucks.

2019 MARYLAND - MAY 2019
Food & Wine Festivals, Shows & Local Events
events waiting for new dates

May 5, 2019 - Naptown barBAYq - Annapolis, Maryland
CANCELLED FOR 2019.  The Naptown BarbayQ will not be happening in 2019. Thank you for your past patronage.

May 18, 2019 - Somerset Strawberry Festival - Westover, Maryland
New Location: Somerset County Parks and Recreation Fields.  This year our festival is being dedicated in memory of Ronnie Brooks, husband of Carol Brooks, President of the Arts Council Board and Fred Peak, husband of Joanna Peak, Immediate Past President of the Arts Council Board.  The festival begins at 9am right in the heart of Marion Station, Maryland.  Marion Station is a small town located north of Crisfield in Somerset County.  Bring your family to this year's Strawberry Festival for some fun, food, and history. Live music, arts & crafters, food vendors, Little Miss & Mr. Strawberry contest and lots lots more.  (also: )

2016 MARYLAND - MAY 2016
Food & Wine Festivals, Shows & Local Events

events waiting for new dates

May 29, 2016 - Ridgely Strawberry Festival - Ridgely, Maryland
An annual event with craft vendors, strawberry shortcake and other food, games, live music and a parade. Benefits local charitable organizations.

2015 MARYLAND - MAY 2015
Food & Wine Festivals, Shows & Local Events

events waiting for new dates

May 2-3, 2015  Bud Break Tasting Room Event - Dickerson, Maryland
Join us in celebrating the unofficial start of our summer season. New wines released and live music.

May 13-17, 2015  MidAtlantic Wine + Food Festival
Various locations, Maryland
The MidAtlantic Wine + Food Festival has been canceled "indefinitely" as organizers have struggled with declining attendance & unpaid bills.



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