Chestertown, Maryland, is a charming historic town that knows how to relax and unwind. Whether you’re looking for a cozy spot to enjoy craft cocktails or a lively atmosphere for a casual drink, the town’s happy hour scene has something for everyone. Here are the top three places in Chestertown to enjoy happy hour.
Modern Stone Age Kitchen
Artisan Bites & Naturally Fermented Beverages
A truly unique spot blending culinary history with modern flair, Modern Stone Age Kitchen offers a refined take on happy hour. Known for their nutrient-dense, traditionally prepared foods, this family-run eatery also serves naturally fermented wines, sour beers, and craft cocktails with house-made mixers. It’s the kind of place where quality and intention are the main ingredients—and the atmosphere is as inviting as the menu.
Why You’ll Love It:
From sourdough pizza nights to casual wine tastings, Modern Stone Age Kitchen is perfect for those who appreciate good food and great conversation in a cozy, thoughtfully curated space.
The Retriever Bar
Craft Cocktails & Live Music
Tucked in the heart of Chestertown’s Historic District, The Retriever Bar is a must-visit for cocktail and oyster lovers alike. This stylish spot offers an impressive menu of handcrafted drinks, as well as a rotating selection of local beers and wines–plus a raw bar featuring fresh oysters, perfect for pairing with your favorite happy hour sips.
Why You’ll Love It:
With its trendy vibe, live music on select evenings, and the addition of an oyster bar, The Retriever blends laid-back fun with just the right touch of sophistication.
The Kitchen at the Imperial
Upscale Drinks & Small Plates
Located in a historic inn, The Kitchen at the Imperial brings an elevated touch to happy hour. With a focus on fresh, locally sourced ingredients, their small plates pair perfectly with their expertly curated drink menu. Whether you’re sipping a glass of wine or trying one of their signature cocktails, this spot is ideal for a more refined happy hour experience.
Why You’ll Love It:
The blend of upscale ambiance and warm hospitality makes this a go-to spot for those seeking a sophisticated yet relaxed evening out.
Cheers to Chestertown!
Whether you’re in the mood for a craft cocktail, a fine glass of wine, or a classic pint, Chestertown has a happy hour spot for every style. These three venues highlight the town’s unique blend of history, charm, and vibrant nightlife.
What’s Your Favorite Happy Hour Spot?
Let us know where you love to unwind in Chestertown in the comments below or share your top happy hour pick with friends!
