September Date Night Ideas and Events in Maryland

Adults want to have fun too! Here are some events and date ideas that are worth paying a babysitter to come watch your kids while you have some quality time with your partner or enjoy a fun night out with friends.

1 Saturday
Freedom on the Horizon
Living history interpreter Natassia Parker-Gross debuts her one woman show on the extraordinary life of Oney Judge, who escaped in 1796 after spending much of her life enslaved. Q&A session following the play. $20. 6:30-8pm. Historic London Town & Gardens, Edgewater.


jazzfest20185 Wednesday
Chestertown Jazz Festival
Sept. 5–9. Four-day jazz and blues extravaganza featuring performances, events and more. Various locations, Kent County.

Dinner Under the Stars
West Street closes and is filled with cafe tables reminiscent of the open air cafes in Paris and the piazzas of Rome. Live music, special art exhibits and canopy lights. Free, to dine varies. Reservations at participating restaurants strongly recommended. 6pm. West Street, Annapolis.

6 Thursday
Save the Crane Fundraiser
Waterfront celebration featuring live music, creative cuisine, cutting-edge cocktails and more. $40. 6:30-9:30pm. Baltimore Museum of Industry, Baltimore.

9 Sunday
Live music, grape stomping, vineyard tours and more. $16; $10 for designated driver. 11am-5pm. Crow Vineyard & Winery, Kennedyville.

13 Thursday
Taste of the Chesapeake
Unique food, drinks, live raffles, silent auction and more. Tickets start at $100. 6-9pm. Anne Arundel Medical Center Belcher Pavilion rooftop, Annapolis. 443-949-0575,

Zoo Uncorked
Unlimited wine tastings, live music and entertainment, and an art walk with local artisans. 6-9pm. $55; non-member $70. National Zoo, Washington, D.C.

14 Friday
Beer, Ballet and Bubbly
Popular behind-the-scenes series which allows patrons to see a rehearsal of the Washington Ballet’s upcoming productions. A reception follows with beer, sparkling wine and hors d’oeuvres. 6:30pm. England Studio, The Washington Ballet.

15 Saturday
Boatyard Beach Bash
Members of Jimmy Buffett’s Coral Reefers band will entertain in an intimate setting with the backdrop of the Chesapeake Bay. Dinner included. $85. 5:30-10pm. Annapolis Maritime Museum.

Baltimore Seafood Festival
Chow down on crabcakes, crab soup, shrimp salad, local oysters, and of course, Maryland blue crabs. Brought to you by Baltimore’s favorite restaurants. Plus drinks, live music,cooking demos, and an area for families with toys, games, and face painting. $15-$99. Noon-7pm. Canton Waterfront Park, Baltimore.

Oysters On a Tray 6 ORP 020 Thursday
Mermaids Kiss Oyster Fest
Unlimited drink and food tastings, live music, silent auction, oysters and auctions. $105. 6-10pm. Baltimore Museum of Industry. 410-990-4970,

Date Night Movies on the Potomac
Watch “Pitch Perfect” on the Plaza screen; bring chairs. Thursdays through September. Free. 7pm. National Harbor.

Anthony Jeselnik: Funny Games
Comedian Anthony Jeselnik will perform his comedy show. $17-$35. 8pm. The Modell Lyric, Baltimore.

22 Saturday
Downtown Hyattsville Arts
& Ales Festival
Enjoy more than 100 exhibiting artists & artisans, Md. breweries, food trucks, vendors, and live entertainment. Downtown Hyattsville. Free. 6 pm.

 23 Sunday
Chesapeake Oyster & Wine Festival
Top-rated American and International wines paired perfectly with the Chesapeake’s wild and farm-raised oysters and other seafood dishes. $40-$65. 11am-6pm.

27 Thursday
Blazers Bourbon Cigars
Men-only event featuring food, drinks, and cigars. $100. 6-9pm. William Paca House and Garden, Annapolis.

28 Friday
The Understudy
Select days Sept. 28–Nov. 4. Comedy about making plays, the endless cycle of rehearsal, and love. Tickets start at $25. Compass Rose Theater, Annapolis. 410-980-5857,

29 Saturday
Twist & Stout
Fine Wine & Craft Beer event featuring food, music, wine, beer and more. 11am-5pm. Quiet Waters Park, Annapolis. 410-222-7316,

Oktoberfest Live!
Dig out your lederhosen and get ready for unlimited sampling of over 150 beers featuring international, local craft, fall seasonal, marzen and Oktoberfest! Plus great international foods and plenty of live music. 3pm. Power Plant Live, Baltimore.

© 2018 Chesapeake Family Life. All Rights Reserved.