Princess Anne, Maryland

Exploring Princess Anne, Maryland: A Delightful Weekend Getaway

Welcome to Princess Anne, a charming town nestled in the heart of picturesque Somerset County, Maryland. This hidden gem offers a perfect escape from the hustle and bustle of everyday life. With its rich history, scenic landscapes, and warm community, Princess Anne promises a memorable three-day weekend trip for you and your friends. Let’s dive into an exciting itinerary packed with top-rated attractions, delightful dining experiences, and captivating sightseeing spots.

Day 1: Unveiling the Historical Charms

Morning: Soaking Up the Local History

Start your day with a visit to the Teackle Mansion, a historic landmark offering a fascinating glimpse into the region’s past. Built in 1802, this stately home showcases Federal-style architecture and features period furnishings. Take a guided tour and learn about the influential Teackle family, who played a significant role in Princess Anne’s development.

Afternoon: Digging into Local Cuisine

For a tasty lunch, head to the charming Washington Inn & Tavern. This beloved eatery, housed in a beautifully restored 18th-century building, serves up delicious American fare with a Southern twist. Savor their mouthwatering crab cakes, a Maryland delicacy, or indulge in their creamy she-crab soup. You simply can’t go wrong with any choice from their extensive menu.

Evening: A Stroll Through Historic Downtown

As the sun starts to set, take a leisurely walk through Princess Anne’s historic downtown district. Marvel at the well-preserved Victorian and Georgian architecture, adorned with colorful storefronts and inviting boutiques. Don’t miss the chance to explore Charles Drew Heritage Center, which commemorates the groundbreaking African American surgeon and civil rights activist who was born in Princess Anne.

Day 2: Embracing Natural Beauty

Morning: Discovering Janes Island State Park

Escape to nature’s embrace as you venture to Janes Island State Park, just a short drive from Princess Anne. This unspoiled paradise boasts over 2,900 acres of pristine wilderness, including marshes, sandy beaches, and lush woodlands. Rent a kayak or canoe and paddle through the serene waters, immersing yourself in the park’s tranquil beauty. Keep an eye out for the diverse wildlife that calls this area home, such as ospreys, bald eagles, and great blue herons.

Afternoon: A Seafood Feast

After working up an appetite, head to The Red Roost, a local favorite renowned for its seafood offerings. Indulge in the freshest catches from the Chesapeake Bay, from steamed crabs and shrimp to succulent oysters. The Red Roost’s laid-back atmosphere and waterfront views create the perfect backdrop for a satisfying seafood feast.

Evening: Sunset at Deal Island Wildlife Management Area

As the day draws to a close, make your way to Deal Island Wildlife Management Area. This serene spot is known for its stunning sunsets over the Tangier Sound. Find a cozy spot along the shore, relax, and let the vibrant hues of the sky mesmerize you. It’s the perfect way to end a day filled with natural beauty.

Day 3: Immersing in Art and Culture

Morning: Visiting the University of Maryland Eastern Shore

Embark on a cultural journey by exploring the University of Maryland Eastern Shore (UMES). Take a self-guided tour of the campus and appreciate the striking architecture and beautiful landscapes. Don’t miss the Mosely Gallery, where you’ll find intriguing exhibitions featuring works by local artists as well as renowned national and international talents.

Afternoon: A Taste of Southern Hospitality

For a delightful lunch experience, head to The Corner Shoppe. This charming eatery combines a café, bakery, and gift shop, offering a true taste of Southern hospitality. Feast on their mouthwatering homemade soups, sandwiches, and delectable desserts. Take a moment to browse the unique gifts and treasures that adorn the shop, making for a memorable dining experience.

Evening: Maryland Wine Tasting

No trip to Princess Anne is complete without indulging in the region’s wines. Visit Bordeleau Vineyards & Winery, a family-owned winery that produces award-winning wines. Take a guided tour of the vineyards and learn about the winemaking process. Afterward, indulge in a wine tasting session, where you can sample their exceptional vintages while enjoying picturesque views of the surrounding countryside.

As your three-day weekend adventure comes to an end, you’ll leave Princess Anne with unforgettable memories and a newfound appreciation for this charming town. Whether you explored the local history, immersed yourself in nature’s beauty, or indulged in the arts and culture, Princess Anne offers a delightful escape for friends seeking a unique and enriching getaway.

Please note that due to the current circumstances, some attractions and restaurants may have modified hours or operations. It’s always recommended to check their respective websites for the latest information.

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