Menu of Caddyshack Bar and Grill in Oakland, Maryland, USA

Menu Overview

Caddyshack Bar and Grill, nestled in the heart of Oakland, Maryland, delivers a robust American dining experience infused with the charm of a local golf course bar. The menu stands out for its solid selection of handhelds, starters, and small plates, each crafted to satisfy diverse palates without overcomplicating the dining experience.

Among the handhelds, the Turkey, Bacon, Swiss sandwich on a Kaiser roll is a definitive highlight. Its fresh layers of hand-carved turkey paired with crisp bacon and melted Swiss bring a classic deli feel elevated by quality ingredients. Meanwhile, the Crab Cake Sandwich captures the essence of Maryland’s celebrated seafood scene—served simply with lettuce and tomato, it balances delicacy and flavor with finesse. For those seeking plant-based options, the Beyond Burger offers a satisfying, flavorful alternative wrapped in a Kaiser roll, catering thoughtfully to vegan and vegetarian diners.

The starters are equally compelling. Jalapeno poppers and fried pickles pair perfectly with house-made ranch, delivering just the right kick and crunch as an appetizer. The Crab Dip accompanied by soft pretzels stands out as a rich, smooth start, highlighting local seafood in a communal dish. Pub fries topped with bacon and beer cheese, alongside the giant pretzel smothered in beer cheese, underscore the tavern atmosphere that Caddyshack embodies — comforting, hearty, and designed for sharing.

Small plates such as pepperoni flatbread and mac & cheese with fries focus on familiar, beloved flavors done well. Popcorn shrimp served with fries adds a touch of crispy seafood indulgence without overwhelming the palate.

Customer feedback underscores the quality and warm ambiance Caddyshack delivers. From the perfect chicken wings to attentive service—often managed single-handedly by skilled staff like Jenny—the experience is elevated beyond food alone. The outdoor seating accommodating guests and pets alike further enhances its welcoming vibe.

What truly resonates about Caddyshack Bar and Grill is its balance of casual yet thoughtful American fare. The dishes are straightforward, highlighting fresh, quality ingredients and classic flavor profiles, whether in the grilled cheese on sourdough or the medium-rare T-bone steak with blue cheese crumbles praised by diners. The atmosphere effortlessly blends golf course relaxation with neighborhood bar camaraderie, making each visit feel like more than just a meal—it’s a genuine community experience.

In sum, Caddyshack Bar and Grill's menu is a well-curated tribute to American comfort food, presented with care and a distinct local flair. Whether you're stopping by for a quick grilled cheese or indulging in crab dip and pub fries, the flavors and ambiance here make it clear why it’s a favorite spot in Oakland.