Get cozy at Talbot County’s eateries anytime of year. You don’t have to wait for Valentine’s Day to enjoy a romantic escape with your significant other. Here in Talbot County, you’ll find plenty of choices to get cozy – from chic bistros and historic taverns, to authentic Italian and fresh-from-the-Bay seafood – whatever your fancy, we know where to go. Here are a few recommendations. Please note, reservations are strongly encouraged.
EASTON
Bas Rouge
19 Federal Street | (410) 822-1637
The country’s top culinary press has showered this exquisite restaurant with acclaim. With staff boasting pedigrees from stellar institutions like New York City’s Le Bernadin, it’s no wonder it’s become a Mid-Atlantic dining destination. In 2024 the James Beard Foundation recognized Executive Chef, Harley Peet as Best Chef: Mid-Atlantic. Chef Peet turns out extraordinary dishes, tapping the world’s very best everything in season, including white truffles, to create culinary masterpieces. You can choose from more than 500 labels of the world’s finest wines to accompany your meal. HINT: If planning a proposal, let them know ahead of time so they can make the event extra special.
Hunter’s Tavern
101 E. Dover Street | (410) 822-4034
The patio out front of the Tidewater Inn is ideal for people watching, and it doesn’t get any cozier than a seat by the outdoor fireplace. However, if you really want some privacy, aim for a seat in a nook at the back of the tavern, where you can see but not be seen. The tavern serves coveted Chesapeake fare where fresh from the bay options like crab cakes and oysters are front and center. The wine list includes some more adventurous options, including a zesty (affordable) Albariño from Spain. HINT: Hunter’s Tavern is housed inside the historic Tidewater Inn. Book a room for the night to extend the romance.
Legal Assets
22 S. Harrison Street | (443) 746-2178
This buzzy restaurant housed in a two-story Victorian houses does have quiet corners. Tables for two on the porch or patio are particularly coveted in warm weather, while in winter the marble bar becomes a couples’ favorite. Chef David Clark offers a distinctive menu that infuses classic fare with an Asian flair, creating a menu like no other on the Eastern Shore. Here, the Caesar salad is grilled and given a perky Korean dressing, while the chicken sandwich is given a tempura treatment rather than a traditional batter-and-fry. Cocktails are extraordinary thanks to a mixologist who creates botanical blends and juices in house. HINT: To get really cozy, reserve a table upstairs.
Osteria Alfredo
210 Marlboro Avenue | (410) 822-9088
This trattoria’s location, tucked next door to a multiplex cinema belies its romantic interior where stylish woven lights cast a gentle glow over romantic banquettes flanked by soft ochre walls, making it a date night favorite. Chef/owner Alfredo Ferretti takes on all the classic pastas, including an excellent tagliatelle tossed with an abundance of wild mushrooms. He also specializes in seafood, brining an Italian flair to dishes such as a heaping bowl of steamed mussels in a piquant red sauce (ripe for dipping) and branzino topped with breadcrumbs, lemon, and served in a butter sauce spiked with Pinot Grigio. HINT: Make it a full date night as Easton Premier Cinemas is next door.
Out of the Fire
111 S. Washington Street | (410) 770-4777
Committed to providing interesting and creative cuisine while engaging in environmental and social sustainability, Out of the Fire is located inside a charming historic house. The intimate bar, where a handful of modern mandarin-hued seats can be found, including those at two high top tables, offer a chic hideaway. Creative pizzas, fired from a wood-fueled oven are complemented by fresh salads sourced entirely from local farms. Plus, there are a number of standout dishes perfect for sharing, like the Prince Edward Island mussels, which are served in a spicy tomato-caper broth made for dipping.
HINT: Out of the Fire is a great spot for vegan and vegetarian diners.
Scossa
8 N. Washington Street | (410) 822-2202
Long the standard-bearer of sophisticated dining on the Eastern Shore, Scossa, whose name loosely translates into a cross between “shock” and “excitement,” is all about elevated Italian cuisine. It’s helmed by Chef/owner Giancarlo Tondin,. Originally from northern Italy, Chef Tondin arrived in Talbot County by way of New York, where he cooked in some of the finest restaurants, including Cipriani’s. He brings finesse to dishes like fiocchetti with Gorgonzola pear sauce and tender sauteed broccolini topped with sweet scallops and grilled shrimp. HINT: Getting cozy doesn’t have to be at night, Scossa serves lunch and brunch too!
The Stewart
3 Federal Street | (410) 793-4128
When you conjure an image of a true stately experience, it’s likely to look like The Stewart. Think tartan plaid upholstery, club-style seats, a roaring fireplace and fine oil paintings. This 30-seat dining room, more lounge than restaurant, is the backdrop for one of the most intimate of Talbot County’s dining establishments. Its extensive list of single malt Scotch whiskeys and vintage Champagne is renown on the East Coast. The abbreviated menu features exquisite morsels such as gold leaf and squid ink ravioli. Plus, when you can procure some of the world’s finest caviar, why wouldn’t you? HINT: Scotch and champagne connoisseurs, this is where you need to be!
OXFORD
Anthony’s Restaurant
26342 Oxford Road | (410) 226-1118
Warm the heart with authentic Italian food straight from Italy. Chef/owner Anthony Guessregen has honed his craft over a 50-year career, beginning in the bustling kitchens of New York’s finest restaurants. Chef Anthony believes that food comes down to the ingredients, and he let’s good ingredients do the work.
ST. MICHAELS
Bistro St. Michaels
403 S. Talbot Street | (410) 745-9111
From the moment you step onto the front porch that leads into Bistro St. Michaels, a restaurant housed within a pretty Victorian, you immediately sense this is that kind of place, a decidedly romantic spot. Chef/owner Doug Stewart delivers plenty of French classics like steak frites and coq au vin done right. A fun way to experience the best of the atmosphere is to take a seat at the chef’s counter, overlooking the open kitchen. Order a cheese board loaded with locally made selections from a farm just down the street and you’ve got date night nailed. HINT: Ask for one of their cozy booths when making your reservation.
Inn at Perry Cabin
308 Watkins Lane | (443) 258-2228
Imagine yourself the proprietor of the manor along the famed St. Michaels waterfront. That’s what it’s like to splurge on one of the glittering private glass houses at STARS at the Inn at Perry Cabin, a stunning circa 1816 manor. Oriental rugs, chandeliers and, come chilly weather, plush throw blankets, deck out a trio of hideaways tailor made for two. Attentive staff, serve modern takes on Chesapeake favorites. For another romantic experience on property, take a table inside Purser’s Pub, where in winter months, you can cozy up next to the wood burning fireplace, which the staff faithfully stokes. This is a refined but unpretentious place to sample some of the Chesapeake Bay region’s finest, such as local oysters served with Old Bay aioli. HINT: Enjoy both restaurants over a long weekend together!
Limoncello
200 S. Talbot St, Street | (410) 745-3111
The trattoria and wine bar is located at the center of St. Michaels. With natural stone on one wall, Tuscan yellow on another, and accents as blue as the Tyrrhenaian Sea, you’ll be transported to the Amalfi Coast in Italy. In good weather, aim for a seat out front on the brick sidewalk, a prime spot for people-watching. In cooler weather, cocoon at a quiet table one step down from the bustling main dining room. The kitchen specializes in authentic fare, such as polenta con funghi misti and house made gnocchi tossed with a tangy marina, as well as cacciucco alla Livornese, a seafood stew studded with olives and capers. HINT: They have half price wine days on Mondays and Tuesdays!
Ruse
209 N. Talbot Street | (410) 745-8011
Contemporary coastal cool permeates Ruse. Located in the Wildset Hotel, a trendy boutique property, this restaurant offers plenty of reasons to hunker down for the evening. Standouts include sweet New Jersey scallops dolloped with smoked trout roe. Vegetarians will find plenty to love with a rotating roster of exceptional plates, including dishes like a savory grilled green cabbage dressed in maple-tahini dressing. Linger over after dinner drinks, with treasures like 20-year tawny port from one of the best houses in Portugual. Plus, happy hour is a thing to celebrate with deals like $5 martinis (yes!) along with $2 oysters plucked from the water less than a mile away. HINT: Extend the romance with a night at this spa-like hotel.
Theo’s
407 S. Talbot Street | (410) 745-2106
If it’s the ambiance of an intimate steakhouse you desire, reserve a table at Theo’s. Located in the center of St. Michaels, its location is golden, and so too is its menu, featuring impeccable cuts of beef from bone-in ribeye to a delicate filet mignon. The beauty of this restaurant is that you can dress up or dress down; either way you will feel comfortable in one of the inviting dining rooms, or on the intimate front porch. One of the most romantic dishes on the menu is the Chateaubriand for two, a classic preparation served with a side of béarnaise sauce. HINT: Great place to bring your gluten free partner.
TALBOT COUNTY
Momma Maria’s
4021 Main Street, Trappe | (410) 476-6266
This former general store, a landmark within the village of Trappe, has been converted into a lovely Mediterranean bistro. The menu offers some tasty twists on traditional dishes. Their shrimp and grits takes a Southern favorite and gives it an Italian spin, thanks to creamy golden polenta and a generous dose of crispy pancetta. The attentive bartenders are well equipped to offer riffs on classic cocktails, such as a refreshing limoncello mule. HINT: Ask for a window seat for a romantic nook or snuggle up on a couple of seats at the bar.
t at the General Store
25942 Royal Oak Road, Easton | (410) 745-8402
From Sunday brunch through Saturday dinner, this chic little outpost in a former general store offers modern design and a novel menu. Located in the very center of Royal Oak, a quiet crossroads located between Easton and St. Michaels, the menu leans into the restaurant’s name, T as in tea. Not every offering is tea-infused, but plenty are – from the juicy chai-rubbed roasted chicken to the local greens tossed with sweet tea vinaigrette. The loose tea menu is phenomenal, but so are the many hand-crafted cocktails that are also tea-inspired, such as the Earl Greyhound, a refreshing blend of grapefruit juice and Earl Grey-infused vodka. HINT: Wines by the glass or bottle are also available.
TRAPPE
Blue Waterfront Restaurant
21384 Coopertown Road, Tilghman Island | (410) 886-1170
Casual elegance defines this waterfront gem. In warm weather, ask for a table outside on the waterfront deck, where you can watch working fishing boats haul their catch in for the day. During cooler months you’ll find a serene dining room overlooking the water. Chef/owner Tom Green is serious about using locally sourced ingredients. Dry aged beef, delivered by a nearby farm, makes an appearance in both the deceptively simple burger and the sirloin steak topped with cabernet butter. Vegetables are picked daily from Chef Green’s very own garden and greenhouse. HINT: Arriving by boat? The restaurant is located within the Tilghman Island Inn, which has boat slips available.
Tickler’s Crab Shack & Restaurant
21551 Chesapeake House Drive, Tilghman Island | (410) 886-2121
Located within the Wylder Hotel, an 1898 boarding house turned boutique hotel, this restaurant celebrates the spirit of fishermen who came before us. Menus are built to highlight the freshest local produce, from their on-site kitchen garden to seafood fresh from Tilghman Island’s fishing docks. Indoor and outdoor seating is available, and the restaurant offers a variety of specials and happenings throughout the year including Wine Wednesdays and Oyster Tasting Flights on Saturdays HINT: The property sits on 9-acres of lush grounds surrounded by a private waterfront, so it’s a great spot to take pictures to remember your romantic evening.
