Best events this weekend in Oakland

Date and Time

Sat, 17 Jan, 2026 - 01:00 PM

Location

119 S 2nd St, Oakland, MD 21550-1519, United States

Interested in joining a book club, but not totally down with the idea of being told what to read? The Silent Book Club of Oakland, brought to you in partnership with the Friends of the Ruth Enlow Library, is definitely what the doctor ordered! Choose anyt... Read More

Date and Time

Fri, 16 Jan, 2026 - 05:30 PM

Location

American Legion Post 71 Oakland Maryland, Oakland, Maryland, United States

Tickets on sale now at ticketleap! Two canvases to choose from! The price includes a sketched 12x16 canvas, all supplies and 2.5 hours of guidance! $10 from each ticket purchased goes to the High Mountain Gospel Riders Group for The Run For The Son! The... Read More

Date and Time

Sat, 17 Jan, 2026 - 12:00 PM

Location

6 N Second St., Oakland, MD, United States, Maryland 21550

Join the adventure as we embark on a Dungeons & Dragons quest at the Main Library in Oakland on Saturday, January 17th, at 12 PM! New players are always wanted, so bring friends and family. Don't miss a great session!... Read More

Date and Time

Sat, 17 Jan, 2026 - 10:00 AM

Location

Bougie Bottoms Boutique, 114 S Second Street ,Oakland, Maryland, United States

Join us for a day of new years shopping and new permanent jewelry inventory!... Read More