Sipside Lounge

Located in the heart of downtown Oakland, Sipside Lounge is located in a 100+ year old space that melds mirth, music and merriment in a unique environment - both inside and outside - where Maryland's largest iconic stone fireplace, dating to the 1930's, looms over our new Fireside Patio.  

Sipside is next door to Flipside Sounds, a unique vintage vinyl record store.

Keep an eye out for a special New Years Eve announcement!

119 S. 2nd Street

Oakland, MD 21550


Live Music Friday and Saturday

Proprietors: Pat & Barb Franc

Manager: Tiffany Holtschneider

Mixologist: Butch McConnell

Minors 12 & older welcome until 6pm. After 6pm minimum age is 21.


Sun: Closed

Mon: Closed

Tues: 4-10

Wed: 4-10

Thur: 4-10

Fri: 4-10

Sat: 1-10

Our guiding principle is simple: to give every customer something unexpected (in a good way).

Available for private parties and functions.

Tuesdays are "Ladies Night". All glasses of wine are 25% off, plus unlimited chocolates. 

Wednesdays are "Open Bark Night". Man's/Woman's best friend are welcome on our outdoor space.

Reviews...Google 4.8 / Yelp 5.0

Rachel M...Beautiful setting in downtown Oakland. Great selection of wines and specialty cocktails. The owners were so nice and made us feel so welcomed. My new favorite spot. Will definately be back every time I visit Garrett county.

Dewey S...One of Oakland's best kept secrets. So glad the town actually has a lounge for people to unwind.  The drink and service were great. The ginger in the mules was great,

KLING...Beautiful new clean bar in downtown Oakland. What a nice surprise for our time spent up here. Great drinks, Very friendly staff, a watering hole must stop when you're in the neighborhood.

Amy M...Hidden gem! Staying in Deep Creek for the weekend and we were looking for something to do in the evening (not nightclub-ish). Found that this place had live music, so tried it out. Fantasic! Great beer, wine, spirits selection.

Larry S...This place is awesome. Butch the bartender ia very attentive and makes a good beverage. We saw the Terah Crawford Band play. Both a must do while in Deep Creek Lake.

Live Music!

All Performances 6-9 PM (unless shown otherwise). No Cover Charge.

Performances planned for indoors (Sipside Lounge).

Proudly featuring local artists.  Click on the link below to view the live music lineup...M

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Fireside Patio

Fireside Patio is the outdoor extension of Sipside Lounge, where the iconic 1930's fireplace comes to life again.  It's an environment and experience unlike anywhere else around.
Hear that train a comin'? Hang on for some fun!

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Serving regional craft beers and ales, over two dozen exquisite wines (by the glass/bottle), assorted fine whiskeys and other spirits.  Hand-crafted cocktails that evoke the 100 year history of the space are shaken and stirred by some of Garrett County's finest mixologists.  We also have a mouthwatering charcuterie board (two sizes) featuring an assortment of both imported and local meats, cheeses (including Firefly Farms) and accompaniments.

We have partnered with our neighbor The Vagabond Taproom so you can easily access their menu and order food to be delivered to your table with just a tap on your phone.


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119 S. 2nd Street, Oakland, MD 21550

Tel:  301.533.2960


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