The Best Small Town On The Chesapeake Bay For A 3-Day Weekend
Chesapeake Bay is the largest estuary in the United States, stretching across the Atlantic Coastal Plain in the United States. The bay has shorelines in the states of Maryland in the north, and Virginia in the south. Around 8.9 million tourists visited the Chesapeake Bay in 2021, however, one waterfront town stands out more than others. Although it is only home to 1,020 full time residents, Saint Michaels is teeming with maritime history, a walkable downtown lined with acclaimed restaurants, boutique stores, and local art galleries, and, is the perfect destination for a three-day weekend.
Modern Accommodations
St. Michaels Harbour Inn, Marina & Spa is located on the historic waterfront and is fully equipped with 52 rooms and suits, an on-site restaurant, a spa offering massages, facials, and body treatments, and its own dock with 52 boat slips. The rooms range from standard quarters to waterfront suites with king-sized beds. While only select rooms and suites have private balconies and decks, spa tubs, and wet bar areas, all of the rooms include robes, bathroom amenities, in-room Wi-Fi, and much more.
The Wildset Hotel is listed as one of the top 25 best boutique hotels in the world and has been featured in acclaimed outlets, such as the Michelin Guide and Vogue. The hotel is comprised of 34 unique rooms that are spread across three different historic buildings. Each room is designed with their own features that provide comfort based on each guests needs, with a variety of rooms to choose from that include free standing gas fireplaces, private balconies and terraces, sitting areas within large suites, and soaking tubs.
Local Favorites and Historic Lighthouse
The Fool’s Lantern provides guests with a unique “drink wall” that allows customers to sample 12 draft beers and 24 wines in Saint Michaels first and only self-serve wine and taproom. Customers can taste what they like and then pair their drinks with an item of the full dinner menu or indulge in charcuterie, dips, or sandwiches to share at the table. Additionally, bingo is hosted every Monday night.
The Mill Salon + Apothecary specializes in products such as homemade candles, bath and shower products, jewelry and features work across a variety of mediums from local artists. It also doubles as a hair salon. Chesapeake Bay Outfitters prides itself on its “Shore Style” which it has been outfitting patrons in for more than thirty years. They sell clothes, footwear, and accessories for both men and women for any occasion whether that be a casual gathering among friends, or attire for a more formal event. Visitors can also take home a memento with Saint Michaels branded clothing.
The 1879 Hooper Strait Lighthouse is owned by the Chesapeake Bay Maritime Museum and is accessible visitors of the museum. The lighthouse was built in 1879 as a means of aiding boats navigate the shallow waters of Hooper Strait, a mile-wide passage connecting Chesapeake Bay with Tangier Sound. Floating vessels that omitted light were initially used to light the passage although were too costly as they often had to be replaced.
It was originally situated in the middle of the bay but has since been relocated to Navy Point where it still stands today. The lighthouse is fully preserved and allows visitors to climb the steps, and, through interactive displays, learn how lighthouse keepers attended their station, climb the sea hatch, view the lenses in the lantern room, or stand on the lookout deck at the view across the bay.
Waterfront Parks
Saint Michaels is not without its natural attractions. Muskrat Park may only span a half-acre but has lots of appealing qualities, such as landscaped flower beds and historic cannons. It also has gazebos, benches, and picnics, making it a prime spot in town to enjoy the peaceful park ambiance while taking in scenic views of the harbor and surround Chesapeake Bay. The park is situated by the historic town harbor, on Willow Green Street, only a block off South Talbot Street.
Saint Michaels' trails offer convenient and scenic routes that allow people to hike or bike their way across town without being on the main road. Some trails are fully paved and wind along the western edge of town, such as the Saint Michaels Nature Trail, which begins on South Talbot Street, passing through woods, residential neighborhoods, a covered bridge over a creek (popular for fishing), a horse stable, and cemetery before ending at Bradley Park. It's an easy but lovely jaunt; just 1.3 miles.
A Three-Day Weekend in Chesapeake Bay
Saint Michaels blends the Atlantic Coast with the vibe of an understated resort town. It has something for everyone, regardless of the agenda on their three-day weekend. Whether that be enjoying the modern amenities of a historic boutique hotel, soaking up maritime history, indulging in unique culinary experiences, or relaxing in waterfront parks within the town, Saint Michaels is the best small town to spend three days in the Chesapeake Bay.
