The Stewart is a must-visit. Tucked away like a hidden gem, this cozy, dimly lit bar feels like stepping into a little piece of the Scottish Highlands, with a beautiful design that’s all about the details. Primarily a whiskey bar (with a touch of vintage champagne), they have an extensive selection that will impress any enthusiast. Although their selection of other spirits is limited, the bartenders are incredibly knowledgeable and can guide you to something you’ll love. The service is top-notch—friendly, attentive, and ready to help you find the perfect drink. The sushi and small bites are also delicious. While quiet and upscale at first, it soon warms up into a cozy, welcoming atmosphere where you can chat with locals or just savor the ambiance. It’s not a casual dinner spot—it’s more of a refined lounge experience—but it’s absolutely worth dressing up a bit and treating yourself. Even if you just go for a single drink, the experience and atmosphere make it a highlight of the trip.
For a convenient and welcoming dining experience right at the Tidewater Inn, we highly recommend Hunter’s Tavern. The atmosphere is relaxed and comfortable, and the patio is a great spot to enjoy a meal. The hot crab dip is a standout, and the menu offers a range of hearty options that we really enjoyed. It’s a perfect choice if you want a delicious meal without leaving the inn, and we think you’ll have a great time there. Enjoy!
For a laid-back, old-school pub experience with a modern twist, the Washington Street Pub and Oyster Bar is a fantastic spot to unwind. It’s got that classic pub charm—perfect for catching a football game on their big TVs or just hanging out in a casual, friendly atmosphere. We found the vibe super relaxed—no need to dress up, just come as you are. They have a good selection of beers on tap, including some great local Maryland brews we really enjoyed. The service was friendly and it’s clearly a popular local hangout. While we had some mixed feelings about one dish (those loaded pub chips were a bit heavy for our taste), there’s plenty on the menu and the overall pub fare seems solid. It’s a great place for a casual drink, a snack, or even a laid-back dinner. Grab a seat at the bar or find a booth and enjoy the welcoming, easygoing atmosphere. It’s definitely a spot we’d recommend for a relaxed night out!
Just a quick two-minute stroll from the Tidewater Inn, Legal Assets is a local favorite that’s perfect for a casual bite or a laid-back drink. With its East Coast charm—think a cozy, shingled exterior that looks like an old house—and a big, welcoming bar area, it’s a spot where you’ll feel right at home. Inside, it’s simple and unfussy, and you definitely don’t need to dress up. Whether you’re there to watch a game, grab a beer, or enjoy some really tasty nachos (seriously, they’re a highlight), you’ll find a friendly atmosphere and plenty of locals enjoying the vibe. It’s a great spot for a Friday night drink or a casual lunch and definitely a place we’d recommend checking out.
Conveniently located right on Easton’s main square, just a short stroll from the Tidewater Inn, Scosa offers a comfortable and reliable Italian dining experience. It’s a place where you can enjoy a good meal in a relaxed setting, with reasonable prices and a bit of classic charm. While it may not stand out as the most extraordinary restaurant in town, it’s definitely a solid choice for a pleasant Italian lunch or dinner. In other words, Scosa is a nice go-to if you’re looking for something easy and enjoyable without any fuss. It’s a great option for a laid-back meal, and while it may not be the most unforgettable spot, it’s a dependable and welcoming place to dine.
For a unique and interactive experience, The Wardroom is a standout choice. This spot is part wine bar, part shop, and all charm. With a beautiful and relaxed ambiance, it offers a selection of 24 Italian wines on tap that you can pour for yourself using a card system. With options ranging from just a one-ounce taste or a full glass, it’s a fun and engaging way to explore different wines. The Wardroom also serves dinner, and we found their Diavola pasta to be one of the best meals we had in Easton—absolutely delicious and well worth the slightly higher price point. The wine prices themselves are quite reasonable, and you can also purchase bottles with a corkage fee if you’d like to enjoy them on-site. The staff are welcoming and take the time to explain how everything works, making it a memorable and interactive experience. Whether you’re stopping in just for a glass of wine or staying for a full dinner, The Wardroom is a delightful place to unwind and savor great food and drink.
If you’re up for a splurge, we highly recommend Stars at the Inn at Perry Cabin. Set in the charming waterfront town of St. Michaels, this historic Chesapeake Bay estate exudes coastal elegance and was even featured in Wedding Crashers. Even without a dinner reservation, it’s worth stopping by for a drink and a walk around the grounds or a cozy fireside chat. The restaurant offers a seasonal three-course prix-fixe menu that highlights regional flavors with refined execution. Dishes change throughout the year, but we especially enjoyed the steak, shrimp and grits, and a light peaches-and-cream cake. The dining room’s large windows overlook the water, offering stunning views of sailboats drifting by. Dinner runs about $125 per person, making it ideal for a special occasion. Lunch is available on select days for a more casual visit. It’s a memorable way to experience Chesapeake charm with a touch of luxury.
If you’re looking for a super casual, down-to-earth breakfast spot, Breakfast in Easton is a real hidden gem. It’s just a short walk from the Tidewater Inn and has that charming, hole-in-the-wall vibe—like having breakfast at a no-frills, old-school family café. Just a heads-up: it’s cash-only—no cards, no ATM—so bring cash or a check. The food is incredibly affordable (just a few bucks for a plate) and really tasty. It’s simple, classic breakfast fare—eggs, bacon, pancakes, toast. The service is laid-back and a bit slow, and it’s definitely not fancy or luxurious, but if you go in knowing you’re there for a no-frills, cozy meal, you’ll have a great time. It’s all about the delicious, budget-friendly food and that little bit of hidden charm tucked away down a brick alley. Definitely worth a visit if you’re up for a laid-back breakfast adventure!
While you’re here in Easton for the wedding, we definitely recommend starting at least one morning at Rise Up Coffee. It’s a wonderfully laid-back spot with outdoor seating that’s perfect for enjoying Easton’s beautiful weather. You’ll find shaded areas and a casual, walk-up ordering vibe that makes it an easy, relaxed way to start the day. If you’re a coffee lover, you’ll enjoy their Americanos, which are well-crafted and delicious. And if you’re up for a hearty breakfast, try the Sunset Burrito—it’s a standout choice. Skip the avocado toast and go straight for the burrito if you’re deciding between the two! We hope you enjoy this local gem as much as we did. Enjoy your coffee and the relaxed Easton vibe!
If you’re looking for a coffee spot with a beautiful atmosphere and charming design, Weather Gauge Coffee is a great choice. The interior is lovely, with traditional wood paneling, good music, and even a movie playing while you wait. It’s definitely a cozy place to hang out, and it’s quite popular with the local community. Now, a little heads-up for serious coffee drinkers: we found that the espresso-based drinks, like the Americanos, were a bit over-extracted and on the bitter side. So if you’re particular about your coffee or prefer a more refined espresso flavor, this might not be the top pick. However, if you’re going for something flavored or more like a sweet specialty drink, you’ll probably still enjoy it. In short, if ambiance is your priority, Weather Gauge is a delightful place to relax. But if you’re after the best-tasting coffee, you might want to head to Rise Up Coffee instead. Either way, it’s a charming stop!
If you’re looking to unwind during your stay, the Terrasse Spa at the Tidewater Inn is a wonderful little retreat. It’s definitely on the smaller side, so think of it as a cozy, intimate spa rather than a full-day luxury spa experience. But what it lacks in size, it more than makes up for in comfort and quality. Attached right to the hotel, it’s super convenient if you just want to slip in for a treatment. They offer a variety of services like facials and massages, and the massages we had were absolutely fantastic—definitely a 10 out of 10 recommend. They also provide really comfortable robes and slippers, and you can even add on a little champagne or other drinks to make it extra relaxing. Overall, it’s a lovely, intimate spot to get a bit of pampering without having to leave the inn. Perfect for a little relaxation during your stay!
For anyone who loves wandering through a good bookstore, Flying Cloud Booksellers is a charming little haven just a short walk from the hotel. The store has a bright, airy, and impeccably clean feel, blending that old-fashioned, cozy bookstore charm with a modern touch. You’ll find a wide selection of books here—everything from travel and culinary sections to politics, history, fiction, and a fantastic children’s area. It’s the kind of place where you might stumble upon a book you haven’t seen anywhere else. Plus, the staff is friendly and ready to help or chat about your next great read. All in all, it’s a delightful spot that’s super close by—about a five-minute walk off the main square—so it’s perfect for a leisurely browse. Definitely worth a visit!
If you have an eye for design or just love mid-century modern style, The Modern Bulldog is an absolute must-visit. The store is filled with authentic mid-century pieces—think gorgeous Eames chairs and an array of beautifully curated furniture that feels like stepping into a design lover’s dream. The owner, TJ, is incredibly welcoming and one of the nicest people you’ll meet. He went out of his way not only to make us feel at home in the store but also to share local tips and recommendations. It’s a concentrated treasure trove of mid-century gems and absolutely worth a stop if you appreciate beautiful furniture and great hospitality!