Upcoming Oakland Events

Check out what's happening all around Oakland, MD

Saturday Night w/ Ben Benson!

Sat, 01 Mar, 2025 at 07:00 pm 17869 Garrett Highway Suite A, 21550

Relax, Reconnect & Rejuvenate: A Couples' Massage Workshop

Fri, 28 Feb, 2025 at 06:00 pm Jitterbug Movement Studio

Ancient Games: A Hands on Look

Sat, 08 Mar, 2025 at 01:00 pm 6 N Second St., Oakland, MD, United States, Maryland 21550

Dungeons & Dragons

Sat, 15 Mar, 2025 at 12:00 pm 6 N Second St., Oakland, MD, United States, Maryland 21550

Winter Sports Awards

Sun, 16 Mar, 2025 at 06:00 pm Southern Garrett High School

Happy Retirement Jim Sisler!

Thu, 27 Feb, 2025 at 01:00 pm 1862 Maryland Hwy Mountain Lake Park MD 21550

Drag Queen Bingo!

Sat, 26 Apr, 2025 at 06:00 pm Oakland Elks Lodge #2481 USD 34

Janice Ray @ Average Joe's!

Fri, 28 Feb, 2025 at 07:00 pm 17869 Garrett Highway Suite A, 21550

Spring Painting Party

Wed, 12 Mar, 2025 at 04:30 pm 706 East Alder Street, Oakland, MD, United States, Maryland 21550

A Thirst For Art at Stonecroft {Cosmic Cheer Fundraiser}

Tue, 04 Mar, 2025 at 05:30 pm Stonecroft Manor

5th Annual Anything Goes Yard Sale & Makers Market (to benefit local scholarships)

Sat, 26 Apr, 2025 at 09:00 am Mountain Fresh Farmers Markets, Oakland, Maryland

Shiitake Weekend 2025!

Sat, 19 Apr, 2025 at 10:00 am 530 Lynndale Rd, Oakland, MD, United States, Maryland 21550

A Thirst For Art at Stonecroft {Highland or Cowgirl Boots}

Tue, 18 Mar, 2025 at 05:30 pm Stonecroft Manor

AYCE Buckwheat Cake Breakfast

Sun, 02 Mar, 2025 at 11:00 am 3 S First Street, Oakland, MD 21550

Created for Good

Fri, 25 Apr, 2025 at 03:00 pm Haley Farm Inn and Retreat Center, Garrett Highway, Oakland, MD, USA Free

A Series of Knitting Classes at the Main Library

Mon, 03 Mar, 2025 at 06:00 am 6 N Second St., Oakland, MD, United States, Maryland 21550

Big Bucks Bingo

Sun, 09 Mar, 2025 at 02:00 pm Southern High School

3rd Annual Mountain Royal Board Sale

Sun, 06 Apr, 2025 at 12:00 pm 771 Kings Run Road, Oakland, MD

A Series of Knitting Classes at the Main Library

Mon, 31 Mar, 2025 at 06:00 am 6 N Second St., Oakland, MD, United States, Maryland 21550