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The Oak Tavern

4.0 (8 reviews)
Open • 11:00 am - 11:00 pm

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5 months ago

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9 months ago

They have amazing live music, cold beer and good food. Pizza is excellent and I love their Ruben.

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Woodruff’s On Second - Inside near bar

Woodruff’s On Second

5.0(5 reviews)
9.4 mi

I was recently invited to participate in a trivia contest at Woodruff's, a cocktail bar in the…read moreheart of beautiful Odessa. Having recently opened, I'd never heard of the joint. A good friend told me, though, that the cocktails were exquisite and that there was a waiting list for limited memberships. Needless to say, I was intrigued. I was immediately impressed upon entering. Plenty of comfortable seating (we're talking couches and easy chairs), soft ambient lighting, and a kind of quiet mystical aura make it a charming spot to gather with friends and discuss the latest Love is Blind or sit quietly by yourself, writing the poetry of your soul. The two drinks I had were, indeed, fabulous. They have beer and wine as well. Some snacks, too! The drink menu is not extensive, but it is ever-changing, like a good speakeasy will do. The bar staff were all super friendly, helpful, and adept at making spectacular concoctions. The place is open to the public but they also have memberships which gets you a free drink each month and other perks. One in particular is that you get your very own drawer, all of which are located on the front of the bar. I have no idea what a member does with his very own drawer but i find that I am beguiled and must have one for myself. Alas, there is a waiting list, but someday...

We came here on our trip to Missouri. The town of Odessa is small and home-like feeling. We felt…read moreright at home when we entered the doors. The decor is artfully chosen. We enjoyed the gin spring tease cocktail and a smoked old fashioned. The bar tender was very nice and conversational. The speakeasy feel is very comforting. The service was very personalized. Would 12/10 recommend if you want to spent a nice evening with family or friends in a comfortable setting having top-tier hand-crafted cocktails.

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Woodruff’s On Second - Outside

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Woodruff’s On Second - Inside seating

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Woodruff’s On Second - Spring tease gin drink

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Spring tease gin drink

The Oak Tavern - tradamerican - Updated October 2026

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