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    The Checkmate Inn

    4.0 (24 reviews)
    InexpensiveBeer Bar
    Closed 12:15 pm - 4:00 am (Next day)

    The Checkmate Inn Photos

    THE CHECKMATE INN ATMOSPHERE

    What's the vibe?
    Casual
    Loud
    Outdoor seating
    Good for groups

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    9 years ago

    If you like jerking off, you'll love this bar!!! Never felt more at home. Honestly go here.

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    Review Highlights - The Checkmate Inn

    What can I say about the 'Mate besides it's my most favorite bar in the history of ever

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    Portside Bar & Grill - Chicken Caesar wrap with fries (onion rings for my sister across the table)

    Portside Bar & Grill

    3.0(72 reviews)
    2.8 mi
    $$

    Visited this establishment for lunch with my family after hopping off the Port Jeff Ferry. We were…read morein search of a place to eat that welcomed dogs as we were traveling with my Pomeranian, and saw a sign outside the patio that said Portside was dog-friendly so in we went. The lady at the counter (Kelly, I think?) was incredibly friendly, very personable, was happy to chat with my very talkative daughter, gave us recommendations for what's popular to eat at Portside & gave us a great recommendation of a place to get some ice cream after lunch, and even offered us a cup of ice water for my pup. We grabbed a table outside on the patio & ordered our food. We only waited about 15-20mins after ordering before all our plates and drinks came out. Everything tasted fantastic. The fries were crispy on the outside and fluffy on the inside, and my Chicken Caesar wrap was one of the best I've ever had. My dad had cobb salad that looked amazing, sis ordered the portside burger w/ side of onion rings that was really delicious, and hubby & daughter split a chicken fingers basket. We left nothing on our plates when we were done. The food was that excellent. Next time we visit Port Jefferson, we will be back to Portside Bar!

    This should not be classified as American bar and should be classified as a dive bar…read more The bartenders are usually friendly. The place stinks like cigarettes inside and out. The food is acceptable, but there's so many other options. Been there a couple times. Always has a trashy crowd and someone gets in a fight. On the plus side I did once get invited to some drunk ladies Halloween party that she has every year in Port Jeff?!?

    Photos
    Portside Bar & Grill - Dining area

    Dining area

    Portside Bar & Grill - Calamari appetizer.

    Calamari appetizer.

    Portside Bar & Grill - Pup on the Patio

    See all

    Pup on the Patio

    The Checkmate Inn - beerbar - Updated August 2026

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