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    Old Skool Brewing

    5.0 (3 reviews)
    Closed 4:00 pm - 11:00 PM

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    3 years ago

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    7 years ago

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    8 years ago

    Great Place! Great Beers! Great Owners! Great bartenders/maids! Go there! Great Décor!

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    Cross Country Brewing

    Cross Country Brewing

    4.3(7 reviews)
    55.2 mi

    Tiny little spot in a tiny town…read more. We immediately loved the feel of this place as the locals in the bar were welcoming. We ordered a flight of beer to try some different styles and the beers were ok at best. The favorite of the bunch was probably the chili beer. All in all loved this place, loved the hospitality and we'd come back just for that and maybe try some of the other beers (maybe they're better)

    You know that scene in western movies where the wayfaring stranger enters the saloon, all…read moreconversation falls to silence, and every head in the place turns to stare at him? That's Cross Country Brewing, or at least that was my experience of it. After a long day of driving, me, my girlfriend, and my mother were in the mood for a beer or two, so we jumped when we saw that there was a brewery in town. Glendive, after all, isn't exactly a metropolis with microbreweries at every intersection. Indeed, Glendive (or at least Cross Country Brewing) fit the stereotype of the hostile small town that doesn't much like outsiders. As soon as the three of us walked in we were greeted with that ominous silence and a blank, "What do you expect from me?" look on the face of the thin, bearded, ballcap'd bar tender. No "Hi" "What can I get for you?" "I recommend our famous..." etc. Nope. We picked our beers from the chalkboard menu, ordered them, he poured 'em, and then pushed them over to us with an empty, emotionless stare. I didn't get it. We just looked like normal people, not the Addams family. Why the random unfriendly attitudes? It didn't matter how kind or full of smiles we were, it was like our very presence was an insult to the establishment. Geez, sorry we were trying to give you our money. We promise not to bother you again.

    Photos
    Cross Country Brewing - Outdoor patio

    Outdoor patio

    Cross Country Brewing - Front entrance at sunset

    Front entrance at sunset

    Cross Country Brewing - Stout brew

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    Stout brew

    Boots Bar & Grill - Club Sandwich and White BBQ Chicken

    Boots Bar & Grill

    3.7(236 reviews)
    51.7 mi
    $$

    We ate here four times during our visit to Theodore Roosevelt National Park, and if that doesn't…read moretell you how good it is, I don't know what will! lol We tried the PB&Jelly Time burger, the fish n chips, the chicken bacon ranch sandwich and the white bbq chicken sandwich - all were hot and fresh, deliciously seasoned and well balanced. We also fell in love with their french fries. They were just so good! Crispy on the outside, seasoned perfectly, and light and fluffy on the inside. They also have a ton of dipping sauces, so if you're a dipping sauce fan like I am, try them all! I absolutely loved having my cocktails served up in a giant cowboy boot glass! The food and drinks were great, the waiters were easy going and personable - the service was fast too! The inside of the restaurant is like walking into an old western saloon - They've got saddles and other horse tack hanging up everywhere, and they have wagon wheel style tables and live edge wooden tables too - so cool! Totally recommend this place for anybody visiting Medora or just passing through!

    Looking for a bite to eat in town and ran across Boots Bar & Grill. When you enter the restaurant…read moreyou see a sign to seat yourself. You can choose a table, hi top and of course the bar. We found a table towards the back. Waitress came over quickly took our drink order and was back to take our dinner order. Waitress was very sweet, busy taking orders and bussing her tables. But service was great. I ordered the fried chicken sandwich with a side salad $ 2.00 up charge, but very fresh. Sandwich was over cooked and very salty. My husband order the fettuccine Alfredo with chicken which he truly enjoyed as well as a cold beer.

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    Boots Bar & Grill
    Boots Bar & Grill - SW egg rolls

    SW egg rolls

    Boots Bar & Grill - Exterior of Boots Bar & Grill

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    Exterior of Boots Bar & Grill

    Heiser's Bar & Casino - Western bacon burger

    Heiser's Bar & Casino

    4.4(19 reviews)
    0.2 mi
    $$

    This place in inbetween some steak houses and I thought I would try it, walked in place was pretty…read moreempty but it was good the waitress greeted me and I sat down and ordered a drink, looked at the menu for a min and decided to order a western burger and some hot wings... hot wings came first and I was expecting them not to be really good but I was shocked they were amazing.. and then my burger came and it was big and looked amazing.. The food was amazing and the place was really nice and was nice and peaceful, for a really small town I was pretty shocked on the service and the food. I will definitely go back if I come back Into town

    Solid memories of my two stops in here while I was in town…read more The pizza here is locally famous, so I'd heard it about it from coworkers long before I got to town for work. Someone from a company we work with in the area had been in town for months and become a regular here, so my 2nd visit was even better. Grab a Cold Smoke Scotch Ale on tap for an excellent Montana-local beer on tap. Other good beers on tap are available if you want to stray from there. On my 1st visit, someone recommended the tenderloin steak tips, so I decided to save the famous pizza for the 2nd visit. Good call - the steak tips were solid. Wish I could remember what else I ordered. On 2nd visit (with regular leading the way), we went with the cheeseburger pizza, which sounded kinda weird, yet... gotta try something new, soooo... we did! And it was awesome. So good - never had anything like it before. Got cheese curds on the side, which were also stellar. Dined in both times, enhancing the piping hot and fresh experience vs taking something back to the room. Not sure if dining with a regular got me a 5-star experience or if it's always that awesome, but I've thought about this bar several times since I went... so that merits a solid review. I'll definitely be back when I'm back in town.

    Photos
    Heiser's Bar & Casino - Great beers on tap!

    Great beers on tap!

    Heiser's Bar & Casino - Hot wings

    Hot wings

    Heiser's Bar & Casino

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    Old Skool Brewing - brewpubs - Updated May 2026

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