Discover the charm, history, and tranquillity of Maryland’s Eastern Shore
Written By: Teresa Greco
Nestled along the serene shores of the Chesapeake Bay, Talbot County is a quintessential gem on Maryland’s Eastern Shore, effortlessly blending history, natural beauty, and modern refinement. Located just a scenic drive across the iconic Chesapeake Bay Bridge from Washington, D.C., this picturesque county is a breeze to reach for travellers flying from Toronto. Talbot County is home to five historic towns—Easton, St. Michaels, Oxford, Tilghman Island, and Trappe—each offering its own distinct character and charm. With over 600 miles of pristine shoreline, this area invites visitors to unwind, explore, and savour its relaxed sophistication while enjoying the lush landscapes and vibrant maritime heritage.
On a recent trip with a friend, I discovered the best of Talbot County—from waterfront accommodations and unforgettable meals to tranquil boat rides and picturesque small-town streets. Every moment was a reminder of the Eastern Shore’s enduring allure.
The Inn at Perry Cabin: A Timeless Retreat
We began our journey at the iconic Inn at Perry Cabin, a historic waterfront resort in St. Michaels. Built in 1816 by Samuel Hambleton, a naval officer and aide-de-camp to Commodore Oliver Hazard Perry, the inn combines historic elegance with contemporary sophistication. Its Greek Revival design, inspired by Perry’s flagship cabin aboard the U.S.S. Niagara, creates a setting that feels both intimate and timeless.
The inn’s 78 guestrooms and suites offer refined comfort, with fireplaces, marble baths, and French doors that open onto verandas or terraces. Our room featured a private balcony overlooking the Miles River, where we enjoyed peaceful mornings with coffee and stunning views.
Dining at STARS Restaurant was a highlight. Breakfasts were a delicious start to the day, with dishes like the Crab Imperial Omelet and Lemon Blueberry Waffles showcasing the region’s freshest ingredients. Dinner paired Chesapeake flavours with impeccable presentation—pan-seared rockfish, garden-fresh vegetables, and a decadent dessert were the perfect complements to the waterfront setting.
- In the afternoon, we explored the inn’s beautifully landscaped 26-acre grounds. With manicured gardens, winding paths, and bursts of wildflowers, every corner felt like a scene from a storybook. Later, we embarked on a guided bike tour led by Jay Bringberg, a local expert with a passion for sharing St. Michaels’ history. Jay took us through the St. Michaels Historic District, pointing out the town’s colonial architecture, unique boutique shops, and landmarks like the Cannonball House. His stories of St. Michaels’ shipbuilding heritage and its clever defences during the War of 1812—including the town’s ingenious “blacking out the lights” strategy that earned it the nickname “The Town That Fooled the British”—brought its rich history to life.
Exploring the Bay: Sailing and Maritime History
Talbot County’s connection to the Chesapeake Bay is at the heart of its appeal, and we embraced this connection with two unforgettable boating experiences.
One afternoon, we sailed aboard the Stargazer, a 40-foot Friendship sloop captained by Chris, for a private excursion on the bay. The combination of gentle breezes, panoramic views, and Captain Chris’s engaging stories about the region’s heritage made the experience both relaxing and inspiring.
Another evening, we boarded the PATRIOT, a 1920s-style yacht, for a 90-minute Island Music Cocktail Cruise. With live music, drinks, and a spectacular sunset over the Miles River, the voyage felt effortlessly magical.
A visit to the Chesapeake Bay Maritime Museum offered a deeper appreciation of the bay’s influence on Talbot County. Located on St. Michaels’ waterfront, the museum’s exhibits explore boatbuilding traditions, oyster harvesting, and the ecology of the Chesapeake.
Culinary Delights Across Talbot County
Impressivley diverse is Talbot County’s culinary scene, with experiences ranging from refined fine dining to relaxed waterfront meals.
In Easton, we indulged in a sophisticated dinner at Bas Rouge, where the prix fixe menu delivered a flawless balance of creativity and classic European inspiration. The Autumn Salad, with marinated beets, pickled apple, and spiced ricotta, was a refreshing start, followed by the Garganelle, a delicate pasta dish with gulf shrimp. Dessert from the restaurant’s beautifully presented dessert cart was a treat for the eyes and the palate.
At The Crab Claw Restaurant in St. Michaels, we experienced the quintessential Maryland seafood feast. This family-owned waterfront spot has been a local favourite since 1965, and it’s easy to see why. Sitting dockside as the sun set, we savoured the Fried Waterman’s Seafood Sampler, a platter of crabcake, shrimp, clams, flounder, and scallops. The casual atmosphere and lively sounds of mallard ducks and mallets cracking crabs added to its enduring appeal.
The Wildset Hotel: Understated Luxury in the Heart of St. Michaels
Midway through our trip, we checked into the Wildset Hotel, a property brought to life by a pair of D.C.-born sisters whose vision transformed this historic site into a stylish boutique inn and its centrepiece restaurant, Ruse. Opened in the summer of 2021, the Wildset is an infusion of contemporary style into a backdrop rich with historical character. Located on North Talbot Street, the property comprises a quartet of thoughtfully renovated 19th-century buildings, blending vintage appeal with modern comfort.
Our room was bright and inviting, with a freestanding gas fireplace, crisp Parachute bedding, and a sleek bathroom stocked with Grown Alchemist products. Communal spaces like The Garden, with its firepits and cozy seating, provided the ideal spot for relaxing with morning coffee or an evening glass of wine.
The Wildset’s aesthetic balances clean lines and natural textures with antique touches, from wide plank oak floors to custom and vintage furniture. Thoughtful amenities, like complimentary bicycles and local pastries paired with Ceremony Coffee each morning, added to the experience’s restorative atmosphere.
Dinner at Ruse Restaurant was another standout moment. Seafood-focused and modern in its approach, Ruse captures the spirit of the Chesapeake with offerings like freshly shucked oysters, seared scallops, and Rock Shrimp Tagliatelle. The lively atmosphere and innovative dishes make it a dining destination in its own right, perfectly complementing the Wildset’s relaxed yet refined ambiance.
Wine Tastings and Local Finds
Talbot County’s craft beverage scene added another layer of enjoyment to our trip. We visited Lyon Rum, where we sampled small-batch spirits while learning about the distillation process. Our visit to St. Michaels Winery was a highlight, with its inviting tasting room set in a renovated flour mill. We sampled favourites like the Long Splice, a crisp blend of Seyval and Chardonnay, and the fruity Gollywobbler Red, paired with warm hospitality from the staff. The nautical-inspired atmosphere and locally sourced wines made this an unforgettable stop.
Between tastings, we explored St. Michaels’ boutique shops filled with nautical-inspired décor, handcrafted jewelry, and local artwork. These distinctive treasures were the ideal mementos of our adventure.
Charming Stops in Easton and Oxford
No visit to Talbot County is complete without exploring its neighbouring towns. In Easton, we wandered through elegant streets lined with boutique shops like Berrier Limited for fine men’s clothing and admired works by local artists at Troika Gallery.
In Oxford, the historic Oxford-Bellevue Ferry offered a serene crossing of the Tred Avon River. Once across, we treated ourselves to handcrafted ice cream at the beloved Scottish Highland Creamery, a sweet and satisfying finale to our journey.
A Farewell to Talbot County
As we departed Talbot County, I reflected on its unique allure. From the historic elegance of the Inn at Perry Cabin to the understated luxury of the Wildset Hotel, and from culinary delights to tranquil moments on the bay, every experience felt thoughtfully curated.
Talbot County is more than a destination—it’s a place where life slows down, inviting you to savour each moment and reconnect with what matters most. Whether sailing the Chesapeake Bay, exploring historic streets, or indulging in the finest seafood, this is a retreat that leaves a lasting impression.