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    East Side

    5.0 (1 review)

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    10 years ago

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    Lindsay's Tavern

    Lindsay's Tavern

    4.6(5 reviews)
    39.6 mi
    $

    You know how small town taverns go, they are either third places or scary places. This is a third…read moreplace. Met both the owners (dad & daughter) super nice people. Lindsay's actually connects through to Kates on the other side of the building, Kates was hosting a high school reunion while we were in town. Lindsay's is keeping it real, this is a cash bar, ATM available onsite, pool tables, live music featured, drink prices are affordable, and the service is prompt and friendly. Special note, pickle shots are available ;) as long as you don't get too fancy with your drink orders you will do just fine. If you want to stop in for a cold one, engage in some friendly exchange, and/or, catch up on local gossip, here is your best bet.

    This bar is an institution in Pittsfield. It has been around for decades and manages to attract an…read moreeclectic mix of the 'old regulars' and the younger crowd. The original bar looks as it has for as long as I can remember with the old booths lining the wall opposite the bar and a full length bar lined with stools. Despite it's appearance that hasn't changed in years, it still manages to feel clean, bright and inviting. It is connected to Old Boys Pizza by a game room with two pool tables, shuffleboard and a juke box. They have live entertainment as well as a DJ on certain nights. They have a few domestics on Tap but mostly bottles with very reasonable prices. The staff is always very friendly and treat everyone like a regular. If you're in the area it is a must visit.

    East Side - bars - Updated May 2026

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