Why This Spot Is the Best Irish Pub in Chestertown, Maryland

Everyone has a favorite Irish pub. These beloved establishments serve simple, delicious bites and some of the best Irish beer and whiskey. Plus, there’s something special about having a meaningful conversation with the friendly bartender as you enjoy a hearty plate of fish and chips. If you find yourself craving your favorite Celtic comfort food while staying on the Eastern Shore of Maryland, you need to visit O’Connor’s: The best Irish pub in Chestertown, Maryland. For more local restaurant recommendations, be sure to access our free Travel Guide to the Eastern Shore of Maryland!

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O’Connor’s: A Classic Irish Pub in Chestertown, Maryland

A Little Bit of Dublin on the Eastern Shore of Maryland

The main draw of O’Connor’s Irish Pub is the authentic Irish cuisine! Founder Frank Bonass was a native of Dublin, Ireland, until 1990. He brought his passion for honest Irish food and drink to The States! Bonass opened O’Connor’s in 2001, naming it after his wife’s maiden name. Before he passed away, Frank was known for his welcoming personality and long conversations with guests.

Though Frank Bonass no longer mans the bar, his family still runs O’Connor’s and it remains one of the treasured restaurants on the Eastern Shore of Maryland. Washington College students especially love this beloved spot’s delicious Irish food, casual atmosphere, and small-town pub vibe!

A Menu Full of Irish Comfort Food

During a trip to O’Connor’s, expect to enjoy an authentic taste of Ireland. Popular dishes like shepherd’s pie, fish and chips, and corned beef can still be found on the menu. Be sure to try the award-winning crab bisque, too! If you’re thirsty, it has been said that O’Connor’s serves the best pint of Guinness in the region.

Other Chestertown Area Restaurants to Try

Luisa’s Cucina Italia

Luisa’s Cucina Italia is a little slice of Italy in the heart of historic Chestertown. This restaurant and pizzeria is open every day of the week.

Evergrain Bread Company

Evergrain Bread Company is a fantastic European-style bakery serving light lunches, sweet treats, and delicious espresso.

The Fish Whistle

The Fish Whistle is a Chestertown institution! With beautiful waterfront views and very good food, it’s no wonder. This popular spot is open every day of the week.

Get a Taste of the Eastern Shore of Maryland at Brampton Inn!Brampton Inn, near the best Irish Pub in Chestertown, Maryland

After a fun-filled day exploring historic Chestertown, get a good night’s rest at Brampton Inn, a locally owned Select Registry B&B! You’ll find our comfortable and welcoming bed and breakfast in the heart of the countryside, yet less than two miles away from the restaurants and attractions of downtown Chestertown. Each of our bright and airy suites and cottages is appointed with ultimate guest comfort in mind. Our inn features unique amenities like wood-burning fireplaces, a grand front porch, and 20 acres of pastoral beauty. You’ll love waking up to a complimentary gourmet breakfast! Then, later in the afternoon, relax over tea and homemade pastries at our Tea Time and Social Hour. There’s no better way to sit back, relax, and get a taste of the Eastern Shore.

Are you hungry for a trip to Chestertown, Maryland? Check our availability today and start planning your stay!