Caddyshack Bar and Grill
Oakland, Maryland, USA
Caddyshack Bar and Grill in Oakland, MD offers American dining with great cocktails, live music, fast service, and a casual atmosphere. See menu, hours & reviews.
433 N Bradley Ln, Oakland, MD 21550, United States
Caddyshack Bar and Grill
Oakland, Maryland, USA
Overview
Caddyshack Bar and Grill offers a vibrant American dining experience in Oakland, MD. Known for its casual yet lively atmosphere, this American restaurant is a favorite spot for locals and tourists alike seeking comfort food paired with great drinks. Situated conveniently at 433 N Bradley Ln, it combines fast service with a broad beer and cocktail selection, making every visit enjoyable.
The menu features satisfying small plates, fresh salads, and handheld classics like grilled cheese and crab cake sandwiches. Guests appreciate the welcoming outdoor seating and the option to dine in or take out, although delivery is not available. Whether stopping in for lunch, dinner, or a solo bite, this location provides a polished balance of hospitality and flavor.
Gallery
Real shots of the food, atmosphere, and signature dishes at this location.
Local favorites
This casual American restaurant in Oakland is popular for its inviting atmosphere, excellent drinks, and tasty comfort food favorites.
Guests appreciate prompt and friendly table service, even on busy nights with a packed crowd.
A wide variety of cocktails, beers, and spirits complement a diverse drink menu enjoyed by groups and solo diners alike.
Live bands and several TVs create a lively setting that caters well to sports fans and music lovers.
Spacious indoor seating and outdoor areas accommodate families, friends, and tourists stopping by for lunch or dinner.
Conveniently located with free parking and wheelchair accessible entrance, restrooms, and seating options.
Menus highlight popular dishes like fresh salads and grilled cheese, alongside quick bites and small plates.
Experience
This American restaurant shines during relaxed afternoons and lively evenings, offering a range of options to suit various dining preferences and occasions in Oakland.
With its casual vibe, attentive service, and a menu that celebrates fresh comfort food, Caddyshack Bar and Grill invites guests to enjoy everything from solo lunches to festive group dinners. The addition of live music and sports viewing enhances the overall experience. — FoodPlacee editorial note
Gather with friends or family to enjoy popular appetizers like jalapeño poppers and pub fries while catching live music or a game on multiple TVs.
Find a comfortable spot to savor fresh salads or a grilled cheese sandwich, complemented by craft cocktails or a carefully selected beer.
Order quick bites like chili cheese dogs or chicken salad sandwiches for an easy meal at home without sacrificing flavor or quality.
Enjoy the energetic atmosphere from Thursday through Sunday nights, complete with sports, cocktails, and great service until 9:00 PM.
Benefit from free parking, wheelchair accessible entrances and restrooms, making dining comfortable and inclusive for all guests.
Guest sentiment
A snapshot of what local diners frequently mention about this location.
"Good food. Good service. Nice atmosphere. Small portions. Expensive (but everything is in Oakland). I had the "club" and the wife had the chicken salad. She enjoyed the kaiser roll it was on. It appeared there was only one server and she handled the bar too. She gets 5 stars!"
"Hidden gem! The place was packed. Had to grab a dirty table because the servers were so swamped but am so glad we did. Server came over took drink order and food. The burgers are thick and juicy, cooked perfectly and delicious. Sweet potato fries are magnificent and the garlic butter Parmesan wings are amazing! Will definitely be back for more!"
"If you are in the area stop here and get some great food and great service—Erin was our server and she was nothing short of amazing to our family of seven. It’s always refreshing to have a kind, caring, and attentive server. Now let’s talk about this food. Expectations were low—menu is simple, but the food was exceptional. Everything was fresh and delicious and I would come here ten times over as long as they don’t change a thing! This place needs five stars all around! Crab dip with soft pretzel sticks - Five Stars⭐ Cheeseburgers - Five Stars ⭐ Wings (both bone in & boneless) Five Stars ⭐ Pub fries with Beer Cheese - Five Stars ⭐ Turkey, Bacon, Swiss Sandwich - Five Stars ⭐ Everything we ordered was fresh and delicious. 10/10 recommend this place! No photos because we devoured our food as soon as it hit the table."
"This place has great food and the bartender (Ashley) is awesome. Monday night wing night. The wings are by far the best wings around. Friday night steak special is incredible as well. Stop by and see Ashley for a adult beverage, you’ll thank me later!"
"Stopped for a drink and hear Scott Ross play, top notch as always. Also the crab dip was quite good."
"Okay so we stopped here yesterday for dinner. A party of seven consisting of five adults and two kids. There was plenty of parking and the inside was spacious with several tvs. Our waitress was Erin and she was amazing. The food was delicious. I personally ordered the burger with onion rings and a side of ranch. The burger was cooked medium well and was just fresh. Flavored nicely and a nice portion. I could only finish half. The onion rings were the best and that zest sauce is the best onion ring sauce, it packed some nice heat. I sampled one of my mom’s wings and it was fresh as well. The pub fries were also good but I would go with no bacon as it was too much for me but the beer cheese was a 10/10. The pizza flatbread as an appetizer was okay but the crab dip with the pretzels were bomb. Crab dip was flavorful without being salty and the pretzels were amazing as well. Honestly out of this trip this place was my favorite restaurant and I would go back again to try more of the menu. The menu is simple and I love that it is. I don’t like flipping through pages with so many options. They were out of hot dogs when we came but I heard they were amazing. I definitely will come back to try them as well."
"Katelynn was awesome server this afternoon! Our 1st time there and the service was excellent! Very attentive! The wings which our server recommended were better than good! My wife had a burger, again a recommendation from our server. Dad had a bowl of chili! We had Nachos with all the fixings and they were excellent as well! 10/10! They tell me that Trevor R. Is a regular here and he recommended this place!"
"We stopped here on the way back to Deep Creek from Blackwater. It was pretty much the first place on our road trip that was open. Limited lunch menu. BUT we were impressed with the wings and the pub fries were great! I think there was one server working but she did great. We ate outside as we had our dog."
Visit info
Weekly hours below — always confirm with the business before holidays or special events.
| Monday | Closed |
| Tuesday | Closed |
| Wednesday | Closed |
| Thursday | 11:00 AM - 09:00 PM |
| Friday | 11:00 AM - 09:00 PM |
| Saturday | 11:00 AM - 09:00 PM |
| Sunday | 11:00 AM - 09:00 PM |
Open Thursday through Sunday, the bar and grill is ideal for lunch or dinner visits, with guests typically spending up to 2.5 hours dining.
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Menus, prices, hours, services, and availability may change. Please contact the food place directly before visiting or ordering.