This Quiet Chesapeake Bay City Is An Underrated Gem For Nature Lovers

St. Michaels, affectionately known as "The Heart & Soul of the Chesapeake Bay," boasts a spirited maritime heritage and some of Maryland’s prettiest coastal scenes. However, as of 2025, its recreation and natural attractions are largely undiscovered by vacationers and travelers despite all the town has to offer.

For nature lovers seeking a more authentic side of Maryland’s Eastern Shore, St. Michaels is the perfect destination for unobstructed views and laid-back adventures. In place of high-rise hotels lining sandy boardwalks, St. Michaels invites a more genuine and unspoiled view of the coast without the hindrance of massive crowds. Whether relaxing on its shores or exploring its waters, this underrated Chesapeake Bay town promises coastal beauty in its purest form.

Why is St. Michaels Overlooked?

Despite its stunning coastal scenery, St. Michaels often goes unnoticed by nature lovers, overshadowed by more prominent towns and its own commanding history. With just over 1,000 residents as of 2025, this small community is easy to miss, with some assuming it has little to offer due to its size. While larger, busier coastal towns like Ocean City attract visitors with their resorts, boardwalks, and gorgeous beaches, St. Michaels’ slower pace and less developed natural attractions fly under the radar.

The town’s maritime history, ingrained in its culture and heritage, further overshadows its natural attractions. Founded in the mid-1600s as a trading post for trappers and tobacco farmers, the community's first true industry was shipbuilding. By the early 1800s, St. Michaels became highly renowned for its skilled shipbuilders, fostering a new identity. The town's prominence then bloomed further when the community played a role in the War of 1812, defending against British attacks. Local lore famously dubs St. Michaels “The Town that Fooled the British,” as townspeople allegedly misdirected British gunfire by placing lanterns high above the town. Even after the war, when shipbuilding declined, and St. Michaels shifted focus to its oyster industry, these legacies lived on, often eclipsing the town's natural charms.

St. Michaels: The Underrated Jewel of Maryland’s East Coast

While St. Michael’s heritage, historic sites, and seafood scene are absolutely worth exploring, its natural attractions are also vastly underrated. Although the town lacks traditional beaches, its shores and banks are no less gorgeous, offering a more serene and authentic view of the coast. Whether using the town as a gateway to an island adventure, booking a boat excursion to experience the wonders of the Chesapeake Bay, or exploring the waters by kayak or canoe, this maritime town is the perfect escape for nature lovers looking to enjoy the coast without gimmicks and crowds.

Best Outdoor Attractions in and Around St. Michaels

Hop Aboard A Relaxing Patriot Cruise

There are plenty of ways to experience the Miles River in St. Michaels, but excursions with Patriot Cruises stand out for their blend of nature and history. Departing near the Chesapeake Bay Maritime Museum, the tour company allows passengers to sit back, relax, and enjoy views of this Chesapeake Bay Estuary, the largest estuary in the United States.

Set in a replica 1930s steamship called "The Patriot," your time aboard will be nothing short of extraordinary. Passengers can choose between a Happy Hour Cruise or the 70-minute Narrated Historical Cruise, the latter offering unique views of the town’s 200-year-old harborside mansions. The cruises also offer a glimpse at St. Michaels’s marine wildlife, including its famous oysters being harvested by local oystermen and dolphin sightings; the Patriot Cruises tour season will run from April 12th to October 26th.

Hike The Scenic St. Michaels Nature Trail

Back on land, the St. Michaels Nature Trail is a great way to take in a different perspective of the bay and its natural surroundings. Skirting the western edge of town, the 1.3-mile paved route courses past local residences through charming woodlands. However, the main appeal of the hike comes about halfway through, leading hikers to the San Domingo Creek at Waterfront Park. A picturesque branch of the bay, San Domingo Creek is a popular fishing and anchorage site for boaters, nicknamed the “back door to St. Michaels.” After stopping for a photo, picnic, or scenic rest, hikers can cross the waterway at the St. Michaels Nature Trail Covered Bridge before completing the hike at nearby Bradley Park.

Explore St. Michaels By Paddle Or Pedal

Paddling and cycling are other fun ways to explore St. Michaels’ breathtaking landscapes, with countless paths and scenes to explore. For less experienced paddlers, the San Domingo Creek to Hambleton Island trail is a lovely, beginner-friendly option. The route features coves along the way, with colonial homes lining the shoreline. At low tide, the island’s small sandy beach is an additional reward for your journey. Alternatively, more experienced paddlers may prefer the St. Michaels Harbor and Miles River route. The path offers views of the sweeping shoreline along with wildlife viewing opportunities, from Great Blue Heron to muskrats.

Cycling St. Michaels is equally serene, with countless trails to discover. The Oxford/St. Michaels Bike Trail, for instance, is considered one of the best bike routes in the Mid-Atlantic United States. Cyclists can choose from various sections of the 29.6-mile path, whether cruising areas along the water or more inland routes through the two towns. With both communities located in Talbot County, this also allows adventurers to receive free bike, kayak, and canoe rental deliveries from Shore Pedal & Paddle, a local outfitter.

Enjoy A Peaceful Tilghman Island Outing

Just a short drive from St. Michaels, across the Tilghman Island Drawbridge, Tilghman Island is the ultimate place to experience an even more remote and unspoiled side of the Chesapeake Bay. While many are drawn to the beautiful Maryland island for its hospitality, fresh seafood, and exciting events like Tilghman Island Day, its natural beauty, recreation, and serenity are even more worthwhile.

With the advantage of seclusion, the island boasts some of the best water recreation in the state, perfect for exploring the bay and its creeks. The Tilghman Island Marina and Rentals also offer a fantastic selection of gear and equipment, including jet skis, sailboats, pontoons, stand-up paddleboards, kayaks, canoes, and fishing and crabbing gear. Whether soaking in the island’s peaceful surroundings or embarking on a more active adventure out on the bay, Tilghman Island is the perfect addition to your time in St. Michaels.

Take A Rare Chesapeake Skipjack Sailing Tour

St. Michaels is renowned for having some of the finest seafood restaurants in Maryland, proudly reflecting its oystering heritage. For those eager to see this industry in action, local companies like Chesapeake Skipjack Sailing Tours provide an authentic and immersive experience aboard a genuine working skipjack. Like other skipjacks, the H.M. Krentz was built specifically for oystermen working in the Chesapeake Bay. The boats were once the region’s preferred oyster dredge vessels following their introduction in the 1890s, with about 2000 skipjacks on the Bay at one point.

Unlike other boats, skipjacks are designed to navigate the Bay’s shallow waters. Despite this innovation, the vessels faced a significant decline in the early 1900s after oyster prices dipped. Today, around only 30 skipjacks remain in existence, making your time aboard the H.M. Krentz that much more special. While enjoying a ride on the rare vessel, passengers can listen to stories of the area's oystering history while enjoying live demonstrations. The sailing tour offers the perfect combination of relaxation and education, allowing visitors to soak in views while gaining an appreciation of St. Michaels’ history and heritage.

While much of Maryland’s coast has become overrun with resorts, tourist traps, boardwalks, and crowded beaches, small towns like St. Michaels keep the natural spirit of the coast alive. Although beaches and boardwalks certainly have their time and place, true nature lovers know how enchanting it is to stumble upon unspoiled waterfronts, peaceful walking trails, and natural attractions unblemished by human development. Whether picnicking along the shores of Chesapeake Bay, paddling its waters, or riding its waves on a sailing excursion, your time in St. Michaels will feel like a deep and memorable breath of fresh air.