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Home Date Night May date night ideas: Events and things to do

May date night ideas: Events and things to do

Maryland couples looking for a special date night or moms’ night out can enjoy the MD Film Fest, the Bay Blues Festival, a Paint Night and more in the month of May.

Check out our top picks for events worth hiring a babysitter for below.

lucky stiff2 Wednesday

Maryland Film Fest
May 2–6. Catch films and videos from around the world as they debut in Baltimore. Check website for hours, prices and a list of celebrity guest hosts. Various venues, Downtown Baltimore. 410-752-8083, mdfilmfest.com

3 Thursday

Lucky Stiff
Through May 6. Based on the novel, “The Man Who Broke the Bank at Monte Carlo” by Michael Butterworth. An offbeat, hilarious murder mystery musical farce, complete with mistaken identities, six million bucks in diamonds and a corpse in a wheelchair. $23. Check for showtimes. The Colonial Players, Annapolis. thecolonialplayers.org

4 Friday

Star Wars or Spy Wars
Dr. Vince Houghton, Spy Museum historian, explores the intelligence operations in the world of Star Wars. $15. 6:30pm. The International Spy Museum, Washington, D.C. 202-393-7798, spymuseum.org

5 Saturday

Cinco De Mayo Pub Crawl
Drink specials and free cover at all participating venues, along with a map and wristband to guide you to the places you want to be. $10. 1pm. Downtown Annapolis. pubcrawls.com

Derby Day Party
Appetizers, drinks and live showing of the Kentucky Derby. Live and silent auctions, betting and more, to benefit Maryland Theraputic Riding. $150. 5-9pm. Maryland Therapeutic Riding, Crownsville. 410-456-5506, mtrinc.org

Annual Benefit: Building Our Story
Celebrate the story of Chesapeake Montessori. Live music from Crashing Violets, fresh oysters, multi-course dinner, open bar, live auction, paddle raise, raffles and a silent auction. $85. 6-10pm. Annapolis Maritime Museum & Park. chesapeake-montessori.com

Pawject Runway
Drinks, heavy hors d’oeuvres, animals and selfie station with four-legged supermodels, plus live and silent auctions. Proceeds benefit BARCS. $25-$75. 6-10pm. Royal Farms Arena, Baltimore. baltimoreanimalshelter.org

6 Sunday

Sykesville Fine Art & Wine Festival
More than 40 participating artists, demonstrations, live music and entertainment, wine tastings, and children’s activities. Unlimited wine tastings $25. Noon-5pm. Main Street, Sykesville. sykesvillemainstreet.com

A Chorus Light
Dinner served by the Light House Bistro while enjoying the spectacle of “A Chorus Line,” Compass Rose Theater’s final production of the season. $85; $150 per couple. 5pm; show starts at 7pm. Loews Hotel, Annapolis. Compassrosetheater.org

Taste the Music—40th Anniversary Celebration
Commemorate the Columbia Orchestra’s 40th Anniversary. This event will break the boundaries of a traditional concert experience by pairing food and beverages with classical music selections. $100. 5pm. The Columbia Orchestra, Ellicott City. 410-465-8777, columbiaorchestra.org

Rum Running on the Bay
Enjoy a two-and-a-half hour sunset sail on the Schooner Woodwind, while learning about rum, prohibition, sailing, food pairing, cocktail making and more. $89. 5:30pm. Annapolis Waterfront Hotel. 410-263-7837, schoonerwoodwind.com

11 Friday

Pins & Pints
Charity bowling tournament with beer, and music, to benefit the Bowen Foundation for Autism. $200 to play. 6-9pm. Annapolis Bowl. classy.org/event/pins-and-pints/e171653

Totally ’80s Bash
Dinner, live music, live and silent auctions, photo booth, games and more. $150. 6:30-11:30pm. The Westin, Annapolis. annapolisywca.org

12 Saturday

Mother’s Day Tea at Montpelier
Afternoon tea at Montpelier and self-guided tour. Reservations required. Ages 18 and up. $30. 11am and 2pm. Montpelier Mansion, Laurel. 301-377-7817, pgparks.com

King Farm Wine & Music Festival
Wine tastings, live music, local cuisine and children’s play area. $15; $18 at the door. Under 21 free. 2-8pm. Saddle Ridge Community Center, Rockville. Kingfarmwinefestival.com

Bumpin Uglies
The Bumpin Uglies perform. $12. 8-11am. Metropolitan Kitchen and Lounge, Annapolis. mt.cm/bumpin-uglies

13 Sunday

Day on the Bay with Rose
Two hour sail around the Chesapeake Bay while sampling wines. Along with each wine is a paired bite. You will be able to raise the sails, steer the boat or just sit back and relax. $81. 4pm. Annapolis Waterfront Hotel. 410-263-7837, schoonerwoodwind.com

She’s Not Kidding-A Mothers Day Comedy Showcase
A Mother’s day celebration featuring Meshelle, “The Indie Mom of Comedy”. $18; $15 in advance. 7pm. Creative Alliance, Baltimore. Creativealliance.org

14 Monday

Spies and Spirits of the Revolution
Enjoy tales and tactics of the cunning spies George Washington depended on. Old Fashioned cocktail and other whiskey and cider samples from Wigle Whiskey and Threadbare will be served. $25. 6-8pm. The International Spy Museum, Washington, D.C. 202-393-7798, spymuseum.org

From a Haunted Plate
Discover colonial and antebellum food sourcing and cookery from the perspective of an African American chef. The lecture also examines the cooking techniques, cultural transformations, and flavor principles unique to this blend of Western cuisine. 6:30pm. $15. William Paca House and Garden, Annapolis. 410-626-1033, annapolis.org

16 Wednesday

Zoo Paint Night
Guided paint instruction. One drink included with each admission. Ages 15 and older. Registration required. $45. 5:30-8pm. Maryland Zoo, Baltimore. Marylandzoo.org

Click ‘next’ below for more events May 17-31

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