Shelter Island Heights, New York
Exploring Shelter Island Heights, New York
Welcome to Shelter Island Heights, a charming and idyllic destination nestled between the North and South Forks of Long Island, New York. This three-day weekend trip is perfect for a small group of friends seeking a peaceful retreat from the bustling city life. With its scenic beauty, quaint streets, and rich history, Shelter Island Heights promises a delightful escape. Let’s dive into the exciting itinerary we have planned for you!
Day 1: Unveiling the Island’s Beauty
Morning: Discover the Nature Wonder – Mashomack Preserve
Start your day by immersing yourself in the breathtaking beauty of Mashomack Preserve. This 2,039-acre nature sanctuary offers an extensive network of trails, allowing you to explore diverse habitats and observe fascinating wildlife. Be sure to hike the popular Mashomack Point Trail, which leads to stunning overlooks of the coastline. Don’t forget your camera to capture the panoramic vistas and unique flora and fauna along the way.
Afternoon: Sun, Sand, and Serenity – Crescent Beach
Escape to the tranquil Crescent Beach, where pristine white sands and crystal-clear waters await. Unwind under the shade of an umbrella, indulge in a beach picnic, or take a refreshing dip in the Atlantic Ocean. For the adventurous souls, rent a kayak or paddleboard to explore Shelter Island’s coastline from a different perspective. The beach’s laid-back atmosphere and stunning vistas make it an ideal spot to relax and soak up the sun.
Evening: Gourmet Delights – The Tavern Restaurant
After a day of exploration, treat your taste buds to a memorable dining experience at The Tavern Restaurant. Located within the iconic Shelter Island House, this acclaimed establishment offers a cozy and elegant atmosphere. Indulge in their farm-to-table cuisine, featuring locally sourced ingredients that celebrate the island’s bountiful harvest. From fresh seafood to delectable vegetarian options, The Tavern’s menu caters to every palate. Don’t forget to pair your meal with a fine selection from their extensive wine list.
Day 2: Immersing in History and Culture
Morning: Step Back in Time – Shelter Island Historical Society
Get ready to delve into Shelter Island’s rich history at the Shelter Island Historical Society. Located in a beautifully preserved 18th-century farmhouse, this museum showcases artifacts, photographs, and exhibits that chronicle the island’s past. Explore the various buildings on the property, including the Havens House and the Old Jail, and gain insight into the island’s maritime heritage, farming traditions, and notable residents. The knowledgeable staff is always eager to share captivating stories and answer any questions you may have.
Visit Shelter Island Historical Society
Afternoon: Artistic Inspiration – Sylvester Manor Educational Farm
Venture to Sylvester Manor Educational Farm, a historic plantation with deep roots dating back to the 17th century. This unique cultural destination not only preserves the island’s history but also promotes sustainable agriculture and the arts. Take a guided tour of the manor house, stroll through the lush gardens, and learn about the farm’s ongoing conservation efforts. If you’re lucky, you may catch a live performance or art exhibition, showcasing local talent and creativity.
Visit Sylvester Manor Educational Farm
Evening: Waterfront Dining – Salt
As the day winds down, head to Salt, a waterfront restaurant that blends culinary excellence with breathtaking views. Located in the heart of Shelter Island Heights, this charming eatery offers unparalleled vistas of the harbor and beyond. Savor their innovative American cuisine, featuring fresh seafood, locally grown produce, and seasonal delights. With its warm ambiance and impeccable service, Salt promises an unforgettable dining experience.
Day 3: Active Adventures and Lighthouse Charm
Morning: Lighthouse Exploration – Montauk Point Lighthouse
Fuel up with a hearty breakfast before embarking on an adventure to Montauk Point Lighthouse, just a short ferry ride away. Perched on the eastern tip of Long Island, this historic landmark has been guiding ships since 1796. Climb to the top and witness panoramic views of the Atlantic Ocean, Block Island Sound, and the surrounding coastal landscape. Take a leisurely stroll along the rocky beach or explore the museum to learn fascinating stories about this iconic lighthouse.
Visit Montauk Point Lighthouse
Afternoon: Active Pursuits – Kayaking and Biking
Embrace the thrill of outdoor activities by kayaking through Shelter Island’s scenic waterways or biking along its charming paths. Rent kayaks from Shelter Island Kayak Tours and embark on a guided tour, gliding through serene creeks, observing wildlife, and discovering hidden coves. Alternatively, rent bicycles from Piccozzi’s Bike Shop and pedal your way around the island, enjoying its picturesque landscapes and quaint neighborhoods. Both activities offer an exciting way to soak up the island’s natural beauty while staying active.
Visit Shelter Island Kayak Tours | Visit Piccozzi’s Bike Shop
Evening: Farewell Dinner – Vine Street Café
Conclude your three-day journey with a delightful dinner at Vine Street Café, a cozy and intimate restaurant known for its farm-to-table cuisine. Located in an old colonial house, this charming eatery offers an inviting atmosphere and an array of culinary delights. Indulge in their seasonal menu, featuring locally sourced ingredients and expertly prepared dishes. Toast to new memories made with your friends, savoring the flavors of Shelter Island one last time.
As your three-day weekend trip to Shelter Island Heights comes to an end, take a moment to reflect on the memories you’ve created. From exploring nature preserves to uncovering the island’s rich history, this destination offers a perfect blend of tranquility and adventure. Bid farewell to this serene haven, knowing that it will always hold a special place in your heart.