Tilghman Island, a hidden gem nestled on the stunning Chesapeake Bay in Maryland, offers a multitude of activities and attractions for visitors of all ages. A road trip to Tilghman Island will be a guaranteed great time.

Tilghman Island Things To Do Outdoors 

The Chesapeake Bay area, which spans both eastern Maryland and eastern Virginia is well known for its charming coastal areas. Tilghman Island is one of them. With breathtaking scenery and rich maritime history, this tiny island provides a serene escape from the hustle and bustle of everyday life. There are countless ways to explore and enjoy its natural beauty. 

Less than a 2 hour drive from Washington DC, this makes a great weekend getaway from DC. Let’s first take a look at outdoor activities you can enjoy on this small island. 

Skipjack Rebecca T. Ruark

This is the oldest working skipjack in the Chesapeake Bay.  where they can gain insight into Maryland’s oyster trade industry. Skipjacks are traditional sailing crafts specifically designed for dredging oysters in the shallow waters of the Chesapeake Bay. 

Due to her historical and cultural importance, the Rebecca T. Ruark was listed on the National Register of Historic Places in 1985. The vessel has had multiple restorations to keep her seaworthy. Notably, in 1999, she was struck by lightning and badly damaged. Thanks to efforts from the community and supporters, she was fully restored and returned to the water.

Kayaking And Paddleboarding

If you enjoy being out on the water, then you can spend a day on Tilghman Island exploring the Chesapeake Bay by kayak. Paddleboarding is also a great option because this part of the Chesapeake bay has still waters and several miles of shoreline. One of the more popular hotels is the Wylder Hotel Tilghman Island. Not only does it have a heated saltwater pool, but Wylder guests can also use the hotel’s complimentary watersport rentals.

Tilghman Island Marina is a full-service marina that also offers kayak and paddleboard rentals, as well as guided kayak tours. The marina is located at the west entry to Knapps Narrows, which provides access to the Chesapeake Bay. It has 41 slips with a maximum length of 125 feet and a dock depth of 10 feet.

Sailing On Chesapeake Bay

Lady Patty Sail Charters offers sailing trips aboard a classic yacht departing three times daily for the beautiful Chesapeake Bay from Tilghman Island, MD, from April 1 through October 3. The yacht is a 45′ sailing yacht built in 1935 for offshore racing and is USCG inspected for 16 passengers. Additionally, Wade’s Point Inn on the Bay offers private charters and sailing lessons departing from Tilghman Island.

Poplar Island Tours

Poplar Island is located on the Chesapeake Bay, part of Talbot County, Maryland, United States. The island is about a mile off the west side of the St. Michaels/Tilghman Island peninsula. However, there is no direct way to get to Poplar Island from Tilghman Island or St. Michaels because access to the island is restricted to authorized personnel only. 

Visitors can take a guided tour of Poplar Island, which includes a boat ride to the island from the Maryland Environmental Service Tilghman Island dock. The boat ride is approximately 30 minutes long and it is an environmental restoration project. This makes a great day trip for anyone visiting this area. 

Boat Tours On The Chesapeake Bay

A popular way to enjoy Tilghman Island is through boat tours that showcase the island’s picturesque shoreline and diverse marine life. One such example is the Skipjack Rebecca T. Ruark charter mentioned above. Additionally, charter fishing trips offer anglers the chance to reel in some fresh catch while enjoying the serene waters of the Chesapeake Bay.

Wildlife Sightings

There is some stunning wildlife on and around the island, including majestic bald eagles and ospreys. Bald eagles are a symbol of strength and freedom in the United States, making them a must-see for any bird-watching enthusiast. They can be spotted soaring high above the island or perched in trees near the water’s edge. Many times, visitors are lucky enough to witness these skilled predators hunting for fish in the waters around Tilghman Island.

The ospreys are another fascinating bird species commonly sighted on Tilghman Island. Also known as fish hawks, these birds can frequently be seen diving into the bay to catch fish. They are easily recognizable by their distinctive black and white markings and a wingspan that can reach up to six feet. Ospreys can often be observed nesting in tall trees, atop channel markers, or on man-made platforms.

For those interested in exploring the local wildlife, consider taking a boat tour or embarking on a guided birdwatching trip. These excursions provide an excellent opportunity to learn about the diverse bird species inhabiting the area, while also enjoying the breathtaking scenery of the Chesapeake Bay.

Visit St. Michaels Harbor

St. Michaels Harbor is just a short drive away from Tilghman’s Island. There are several things to do in St. Michaels Harbor in the summer. You can enjoy a locally crafted beer at Eastern Shore Brewing, attend fun festivals, shop, enjoy ice cream at Justine’s, and take a sunset champagne cruise, a moonlight sail, a wine tasting cruise, private sailing lessons, private charters, and catering (source: Wades Point Inn on the Bay). You can also enjoy dining at various restaurants such as Ava’s Pizzeria & Wine Bar, Bistro St. Michaels, Limoncello Italian Restaurant, Blackthorn Irish Pub,

The history of St. Michaels dates back to the mid-17th century when it was a thriving shipbuilding and seafood processing center. Today, it’s a bustling coastal community with much to offer visitors who are interested in its maritime past. Stroll through the historic downtown area, filled with beautifully preserved homes, churches, and storefronts, to get a taste of what life was like during the town’s heyday.

The main street in this town is called Talbot Street. Talbot Street is the main road in St. Michaels and is home to a variety of shops, restaurants, and historic sites. The street is known for its charming and picturesque buildings, many of which date back to the 18th and 19th centuries. Some of the notable historic sites along Talbot Street include the St. Michaels Museum, the St. Mary’s Square Museum, and the Chesapeake Bay Maritime Museum. 

Oxford-Bellevue Ferry

For a deeper dive into the history of the area, consider visiting the Oxford-Bellevue Ferry, which has been in operation since 1683, making it one of the oldest privately-owned ferries in the United States.

Go Fish!

Tilghman Island is a great place for people who love fishing. It’s right next to Chesapeake Bay, which has lots of fish like rockfish, bluefish, and flounder. You can fish from the shore or go on a fishing boat trip. There are also fishing guides who can teach both new and experienced fishers some cool tips and tricks. It’s a fun spot to spend a day fishing and learning.

Tilghman Island Things To Do Indoors 

If you happen to be visiting the eastern shore of Maryland when it’s colder or if it rains during your stay, there are also plenty of things to do on Tilghman Island indoors. Let’s take a look.

Lyon Distilling Company

Lyon Distilling Company in St. Michaels, Maryland makes rum and whiskey. Jaime Windon and Ben Lyon started it in 2012. They loved the history of Maryland and its connection to the sea. They use only American sugarcane to make their rum and do it in small amounts the old-fashioned way. If you visit, they’ll give you a free tour and let you taste their drinks. You can also learn how they make their spirits and about the company’s story. The company is pretty popular – it was picked as one of the best rum makers in the U.S. by USA Today for three years.

Tilghman Island Museum

The Tilghman Island Museum is actually called the Tilghman Watermen’s Museum. It showcases the history and culture of the watermen and their families who have lived and worked on the Chesapeake Bay for generations. The museum is a popular attraction that has exhibits on the history of the island, the watermen’s way of life, and the Chesapeake Bay’s ecosystem. Visitors can also learn about the efforts to move the museum into the Lee House and explore the island through virtual tours and images 

Enjoy Spa Experiences

Tilghman Island is home to several spas and wellness centers that provide a range of treatments designed to help visitors unwind and rejuvenate. Let’s take a look at some of the spas that are a short distance from the island. There is one spa on the island itself. Even Keel Wellness Spa is on Tilghman Island that offers a range of services, including massages, facials, and body treatments. If you don’t mind driving to St. Michaels which is very close there plenty of more options.

The Spa at Perry Cabin is a luxury spa located on Perry Cabin, which is a historic estate on the Miles River adjacent to Tilghman Island. The spa offers a range of services, including massages, facials, and body treatments, as well as a steam room, sauna, and relaxation lounge. Also in St. Michaels is Serendipity Salon & Spa. Europa Salon & Spa is another full-service salon and spa located in St. Michaels.

Phillips Wharf Environmental Center

If you’re looking for an educational experience, be sure to make time to visit here. Phillips Wharf Environmental Center is a non-profit organization located in Tilghman Island, Maryland. It focuses on environmental education, aquaculture, and habitat restoration in the Chesapeake Bay. The center offers a range of educational programs, including field trips, summer camps, and after-school programs, that aim to educate and engage people of all ages in the importance of the Chesapeake Bay ecosystem. There is also a public aquarium that showcases the Bay’s ecosystem and its inhabitants, including fish, crabs, oysters, and turtles.

Enjoy The Wonderful Restaurants

Tilghman Island and the surrounding area have great food, especially sea food and fresh fish. Some of the best restaurants in the area include 

One of the notable places is Tickler’s Crab Shack, known for its seafood, soup, and sandwiches. This adorable dockside restaurant offers live music and great service, making for an unforgettable meal. Other options include the quaint Tilghman Island Country Store, where visitors can find casual bites and local treats, or the elegant 208 Talbot for a more upscale dinner experience.

Several of the hotels and inns have great restaurants you can try as well. In St. Michaels the Inn At Perry Cabin has an onsite restaurant. The Wildset hotel which is also in St Michaels has a popular restaurant as well. Take a scenic drive from Tilghman to one of the small towns nearby to explore more food options.

Go Shopping

If the weather is not cooperating and it is not a good time to be outside, check out some of the shops in the area. If you’re on Tilghman Island, you should check out the Tilghman Island Country Store. It’s a cool place with lots of different things to buy. They have snacks made nearby, cool gifts, and everyday things you might need. The people who work there are friendly and can help you find a great souvenir.

Not far from Tilghman Island is a town called Easton. It’s known for its art and many stores. You can find unique clothes, jewelry, and cool old items in Easton’s shops. They also have places that show off the work of local artists. If you get hungry while shopping, there are plenty of restaurants and cafes in Easton. They serve tasty local food.

Things To Do In Tilghman Island

Maryland’s eastern shore is a great place to visit. From exploring the great outdoors to wandering the one historic town after another, everyone can find something fun to do here. Tilghman Island, located on the picturesque Chesapeake Bay in Maryland, is a tranquil destination with a rich maritime history. Easily accessible from Washington DC, it offers a range of things to do for outdoor lovers. Outdoor activities include sailing on the oldest working skipjack, Rebecca T. Ruark, kayaking, paddleboarding, fishing, and witnessing spectacular wildlife like bald eagles and ospreys. 

Visitors keen on history can visit Poplar Island and the Tilghman Watermen’s Museum. Indoor enthusiasts have the option of exploring distilleries, spas, or the Phillips Wharf Environmental Center. Nearby, St. Michaels Harbor boasts historic sites, breweries, dining options, and shopping. Whether it’s nature, history, or relaxation, Tilghman Island and its surrounding areas provide a unique and unforgettable experience.

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