The Ultimate Guide To St. Michaels, Washington D.C.’s Elite Weekend Getaway

St. Michaels, a well-kept secret for Washington’s elite, comes alive during the warmer months with sailing and boating enthusiasts but cooler weather without tourists is an ideal time to explore this small town and beyond. The close proximity to major cities such as Washington D.C., Baltimore and Philadelphia makes it an easy weekend getaway destination for those antsy to get out of the city between the long summer and the winter holiday season.

Situated on the Chesapeake Bay, within an hour and 40-minute drive from Washington D.C., this quaint old town in Talbot County that oozes historic charm gained the name, “the town that fooled the British” during the War of 1812 when it cleverly fended off the British Army from an attack.

Even during the busiest time of the year, St. Michaels doesn’t reach the level of the Hamptons or some other popular beach towns on the scale of bustling liveliness. It’s not the place to see or be seen but to spend a quiet time with family and friends at a slow pace while sailing, cycling, strolling and sharing oysters or the region’s famous steamed blue crabs.

Spring and summer have plenty of water activities and ongoing festivals but fall offers beautiful foliage, atmospheric charm and autumnal festivals such as “Fall into St. Michaels”, OysterFest, and the unmissable Waterfowl Festival – all without large crowds.

WHAT TO DO:

Chesapeake Bay Maritime Museum

The extensive 18-acre museum has a working shipyard where Chesapeake Bay boats are built and restored. There’s also a 1912 buyboat — commonly known as deck boat — where children can play. Hop on the historic river cruise or rent a small boat to explore the waterways.

Booze tasting

There are three wine, beer and liquor tasting places conveniently located within the same block, on and off of Talbot Street. Go to St. Michaels Winery to taste the variety of wines made from grapes from local vineyards; try award-winning beers at Eastern Shore Brewing, the oldest brewery in Eastern Shore; and visit Windon Distilling Company, the place to learn about the production of the hand-crafted American rum using Louisiana cane sugar and molasses.

Walk on Talbot Street

The main street lined with historic houses is neither long nor overly commercial. Instead, inviting eateries and independent stores are found along the street. Drop by Antiques on Talbot for local antique items, especially nautical-themed objects; pick up souvenir T-shirts and stickers at The Preppy Redneck.

Explore nearby towns

Talbot County, which St Michaels is part of, has a number of small towns that are well connected by bike or car for easy exploration. Tilghman Island is a working fisherman’s village set apart from the rest of the county by a drawbridge. Oxford is a small historic town with a working marina.

But of all the small towns in Talbot County, Easton is the most charming and sophisticated. It’s packed with buildings from the 18th and 19th centuries that reflect the rich colonial history of the area. Wander around the atmospheric “The Hill” area founded by freed slaves in the 18th century. It’s one of the oldest African American communities, if not the oldest as some scholars argue.

Throughout Easton, there is an array of delightful cafes and restaurants, vintage shops and independent bookstores. Also, visit Academy Art Museum. This small museum housed in an early 19th century school building displays a permanent collection that comprises old masters as well as modern art. It often hosts exhibitions of local artists.

WHERE TO EAT:

Ruse

True to the local tradition but with a modern twist, Ruse brought a breath of fresh air to the St Michaels’ rather old-fashioned dining scene when it first opened in 2021 at The Wildset Hotel. The welcoming interior is cozy and tastefully designed in the Scandi minimal style.

The simple and unfussy American menu includes crowd pleasing dishes, from burgers to seafood. The popular oyster bar offers a variety of oysters from the Chesapeake and other parts of America.

Sprout

This airy all-day cafe, with an atmosphere of a communal space, serves all kinds of breakfast items and simple dishes, such as acai bowl, granola and baked goods, as well as soup, salads, curry and a vegetarian burger.

All items are made from scratch using local and organic ingredients whenever possible and a lot of items are packaged for easy take-out.

Justine’s Ice Cream Parlour

This old fashioned ice cream shop has been the locals’ favorite since 1987. Classics such as cookies & cream and PB swirl are perennially popular but other options include non-dairy sorbets and seasonal flavors like pumpkin or eggnog.

WHERE TO STAY:

Inn at Perry Cabin by Belmond

Iconic and legendary, it’s a cliché to mention that this hotel, on 26 acres of land with sweeping views of the Miles River, was featured in the 2005 movie, “Wedding Crashers”.

The history of the hotel goes far back to the 1800s when Samuel Hambleton, a naval officer, had the house built after his retirement to St. Michaels in 1816.

Nowadays, the 78 rooms and suites feature water or garden views and are decorated with a mix of furniture from different periods. While keeping the tradition, the atmosphere is crisp and uncluttered — not your granny’s house with a jumble of paisley patterned sofas and arm chairs — and the limited color palette keeps the interior modern.

The hotel comes with an outdoor swimming pool, spa and restaurants. Go to Stars, which offers upscale all-day dining services including afternoon tea. When the weather is nice, it’s a treat to have lunch on the outdoor terrace with expansive water views. Note that the menu is mainly seafood focused.

For casual dining, Purser’s Pub offers a simple menu of finger foods — dips, chicken wings, and sandwiches to wash down with a variety of cocktails and whiskeys. It’s cozy to hang out at the bar or around the fire pit in the courtyard.

For outdoor activities, rent a bike to explore the surrounding areas. If you’re a golfer, there is an 18 hole golf course designed by Pete Dye, the legendary golf course architect. However, the essence and life of St. Michaels is water, after all. The hotel has daysailers available for guests: there are group sails throughout the day or, for something more special, request a private tour that comes with lunch, cocktails and dinner.

It’s an indulging stay for a taste of the quintessential Washingtonian luxury.

Inn at Perry CabinInn at Perry Cabin Resort | St. Michaels, Maryland

The Wildset Hotel

Despite its popularity as a travel destination, St Michaels was strangely lacking in hotel options until The Wildset Hotel came along in 2021. Minimally stylish with an understated charm, the hotel is arranged across four buildings. The main one was the town’s school house built in the 1830s.

Rooms and suites are available with different configurations and sizes. The decor is minimal but most rooms come with a fireplace, balconies and private patios. Parachute beddings and Grown Alchemist bath products are nice touches for added comfort.

The hotel also comes with bike rentals, a sundry room with carefully curated souvenirs and, best of all, its own restaurant, Ruse. This farm-to-table place that serves sophisticated modern American food is a must-visit even if you don’t stay at the hotel.

ThewildsetThe Wildset Hotel