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Caddyshack Bar and Grill in Maryland

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.

4.6 54 reviews $10–20 American Restaurant American · Southern

433 N Bradley Ln, Oakland, MD 21550, United States

FoodPlacee Passport United States · Maryland · 70055
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Caddyshack Bar and Grill

Oakland, Maryland, USA

Salads Grilled Cheese
Rating★ 4.6 / 5
Price$10–20
CategoryAmerican Restaurant
Today 11:00 AM - 09:00 PM

Overview

About This Food Place

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

Photos from Caddyshack Bar and Grill

Real shots of the food, atmosphere, and signature dishes at this location.

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Local favorites

Why People Come Here

This casual American restaurant in Oakland is popular for its inviting atmosphere, excellent drinks, and tasty comfort food favorites.

Fast Service

Guests appreciate prompt and friendly table service, even on busy nights with a packed crowd.

Great Cocktails & Beer Selection

A wide variety of cocktails, beers, and spirits complement a diverse drink menu enjoyed by groups and solo diners alike.

Live Music & Sports

Live bands and several TVs create a lively setting that caters well to sports fans and music lovers.

Group Friendly with Outdoor Seating

Spacious indoor seating and outdoor areas accommodate families, friends, and tourists stopping by for lunch or dinner.

Accessible Location & Parking

Conveniently located with free parking and wheelchair accessible entrance, restrooms, and seating options.

Comfort Food Favorites

Menus highlight popular dishes like fresh salads and grilled cheese, alongside quick bites and small plates.

Experience

When & How to Enjoy This Place

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

Group Dinner

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.

Solo Dining

Find a comfortable spot to savor fresh salads or a grilled cheese sandwich, complemented by craft cocktails or a carefully selected beer.

Takeout for Convenience

Order quick bites like chili cheese dogs or chicken salad sandwiches for an easy meal at home without sacrificing flavor or quality.

Weekend Evenings

Enjoy the energetic atmosphere from Thursday through Sunday nights, complete with sports, cocktails, and great service until 9:00 PM.

Accessible Experience

Benefit from free parking, wheelchair accessible entrances and restrooms, making dining comfortable and inclusive for all guests.

Best for

Lunch Dinner Solo dining Groups Great cocktails Beer selection Live music Takeout

Guest sentiment

What People Feel

A snapshot of what local diners frequently mention about this location.

RO
Robert OfOakland 3 week ago

"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!"

PA
Pamela Abramson 3 week ago

"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!"

AY
Amy Yuhki 1 month ago

"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."

CGS
Coastal Group Services 1 month ago

"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!"

MW
Mark Woodcock 2 month ago

"Stopped for a drink and hear Scott Ross play, top notch as always. Also the crab dip was quite good."

AJ
Aleia Jay 2 month ago

"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."

JS
John Sharpless 3 month ago

"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!"

JT
jessica templeton 3 month ago

"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

When to Visit

Weekly hours below — always confirm with the business before holidays or special events.

Today Closed
Weekly hours
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
Hours may change. Please confirm with the business before visiting.

Best time to visit

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.

Thursday to Sunday, 11:00 AM - 9:00 PM Evenings are great for groups and live music Plan for 45 minutes to 2.5 hours per visit Outdoor seating available for a casual dining experience Enjoy cocktails and beer selection during dinner

On the map

Where This Food Place Lives

Find your way to Caddyshack Bar and Grill in Maryland .

Address 433 N Bradley Ln, Oakland, MD 21550, United States
Phone +1 301-334-2444
Area Maryland
Call Address copied ✓

Questions answered

Food Place Questions

Find answers to common questions about Caddyshack Bar and Grill, including menu options, hours, and amenities to help plan your visit in Oakland, MD.

The restaurant is open Thursday through Sunday from 11:00 AM to 9:00 PM. It remains closed Monday through Wednesday. Hours and availability may vary, so checking ahead is recommended.

Yes, guests can enjoy outdoor seating and takeout options. However, delivery service is not available at this location.

Accessibility features include a wheelchair accessible entrance, parking, restrooms, and seating to comfortably accommodate all guests.

The menu focuses on American comfort food such as salads, grilled cheese, chicken tenders, and wings, complemented by a wide selection of beer, cocktails, and wine. Menu items and availability may change.

Yes, the restaurant provides high chairs and a kid-friendly menu that includes popular drinks like Shirley Temple and food options designed for younger guests.

Free parking is available, including both a parking lot and free street parking to make visits convenient for all customers.

Payments can be made via credit cards, debit cards, and NFC mobile payments, providing flexible options for guests.

Visitors usually spend between 45 minutes and 2.5 hours, depending on dining preferences and events such as live music or sports viewed onsite.

For owners

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Menus, prices, hours, services, and availability may change. Please contact the food place directly before visiting or ordering.