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HomeDate NightOctober date night ideas: Events and things to do in Maryland

October date night ideas: Events and things to do in Maryland

winefestMaryland couples looking for a special date night or moms’ night out can enjoy a live concert, haunted pub crawl, Masquerade Ball and other special events in the month of October.

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

Be sure to take a peek at our full October calendar for more ideas for some end of the summer fun.


 1 Saturday

Dalla Terra Portfolio Wine Tasting
Saturdays weekly. Taste affordable quality wines from Italy’s finest producers. Free. 11am-4pm. Wine Cellars of Annapolis. 410-216-9080, winecellarsofannapolis.com/calendar/october

Haunted Pub Crawl
Guided pub crawl with a long-dead barmaid, a ghost whose beer has a head and other characters. Visit three to four bars and stay in each bar approximately 30 minutes. $22. 9pm. 443-333-4774. Downtown Annapolis. Meeting location TBA. toursandcrawls.com/tours/haunted_pub_crawl

Riverside WineFest at Sotterley
Oct. 1-2. Wine, local beer, live music, demonstrations, art and food for sale plus free mini tours of the 1703 Plantation House and the Colonial Revival Garden. Ages 21 and older with ID for tastings. $25, $20 designated drivers. Sat., noon-6pm; Sun., noon-5pm. Sotterley Plantation, Hollywood. sotterley.org/winefest-sotterley-plantation.htm

Frederick’s Oktoberfest
Oct. 1-2. Bratwurst, Oktoberfest bier, German wines, dancing, music and more. $5-$17. Sat., 11am-10pm; Sun., 11am-6pm. Frederick Fairgrounds, Frederick. 240-599-0660, frederickoktoberfest.com

6 Thursday

Date Night Movies on the Potomac
Watch “10 Things I Hate About You,” rated PG-13. Shown on the plaza screen. Bring chairs. Free. 7pm. National Harbor. Nationalharbor.com

7 Friday

Pumpkins on the Green
Down home, sustainable culinary experience. Taste culinary creations from local farms and bid on items during the auction. $140. 7-11pm. Irvine Nature Center, Owings Mills. 443-738-9200, explorenature.org/center-event/pumpkins-green-ungala-3

Special Historic Hauntings
Through Oct. 29, Fridays and Saturdays. Tour the inside of the haunted James Brice House at night. $10-18. 7:30pm. Historic Annapolis Museum and Store, Annapolis. annapolistours.com/our-tours/historic-ghost-walk

Second City: Free Speech While Supplies Last
An irreverent look at America’s electoral situation with political satire of scenes, songs and improv from Chicago. $30, $25 members. 8pm. Maryland Hall for the Creative Arts, Annapolis. 410-263-5544, marylandhall.org

Baltimore Beer Week
Oct. 7-16. A week-long series of events celebrating locally produced beers and drink specials. Check website for a full schedule of events. Various venues, Baltimore. baltimorebeerweek.com/

8 Saturday

Hops & Harvest Festival
Unlimited tastings of Maryland breweries and ciders, artisans, entertainment and games, local food, take-home event glass and more. Ages 21 and older. Midday tickets, noon-4pm, or twilight tickets, 5-9pm. $40. Columbia Lakefront, Columbia. Hopsandharvestfest.com

annapolis tours

Das Best Oktoberfest
Over 150 domestic, international, and local beers and wines. All you can taste event. Live music, food, games area and more. $39. 2-6pm. M&T Bank Stadium, Baltimore. dasbestoktoberfest.com/baltimore/show-info

Costume Ball
Dress the part of your favorite portrait for an evening of Regency-style dance and light refreshments. Black tie welcome. $25-32.50. 7:30-9:30pm. Riversdale House Museum, Riverdale Park. 301-864-0420, culturecapital.com/event/47122/costume-ball

Blue Oyster Cult
The hard rock band Blue Oyster Cult performs. $45-65. 8pm. Maryland Hall for the Creative Arts, Annapolis. 410-263-5544, marylandhall.org/blue-oyster-cult

Good Beer Festival
Oct. 8-9. Tastings of more than 100 craft brews and a beer garden featuring Eastern Shore breweries. Also live music, games and more. $10-60. 12:30-6:30pm. Pemberton Park, Salisbury. Goodbeerfestival.com

13 Thursday

Sip and Paint
Create original artwork under the guidance of local artist Kim Hovell. Bring your own wine and snacks.​ Advance purchase tickets. $45. 6:30pm. Maryland Hall for the Creative Arts, Annapolis. 410-263-5544, marylandhall.org

16 Sunday

Peter Frampton Raw: An Acoustic Tour
Grammy award-winning Peter Frampton performs. $49-350. 8:30pm. The John F. Kennedy Center for the Performing Arts, Washington, D.C. 202-467-4600, kennedy-center.org/calendar/event/ZRPTF

Click next below for more October date night ideas

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