Illustrations by Joni McKown Jake Rose
Color Shelter Island
Color Our Town COLORING BOOKS
A celebration of the beauty and diversity of America’s Cities & TOWNS
Welcome to Shelter Island
Welcome to Shelter Island, an awesome town packed with fun, adventure, and things to discover! Whether you want to take in the breathtaking views from Crescent Beach, explore the mysteries of history at the Shelter Island History Museum, or play an incredible game of golf at the Shelter Island Country Club, there’s something here for you. Don’t miss Taylor’s Island, where you can snap a selfie with the rustic cabin, and be sure to check out its iconic windmill—it’s unforgettable! From beautiful beaches to wonderful hotels and amazing landscapes, Shelter Island is ready to be your new favorite adventure. Enjoy every moment!
Photo by Jaclyn Vernace
1. Shelter Island
Nestled between the North and South Forks is Shelter Island. Only accessible by ferry, Shelter Island is known for its natural beauty, hiking, biking, birdwatching, and some of the most breathtaking kayaking in Suffolk County. Based on the Manhanset name for the area (Manhansack-aha-quash-awamock, or “an island sheltered by islands”), Shelter Island was acquired by James Farsett in 1638. Over the next 375+ years, the island transformed from an agricultural and fishing settlement into a vibrant summer resort town with subdivisions and homes lining its waterfront. Shelter Islanders have done an outstanding job in maintaining and preserving the Island’s historic locales, gorgeous landscapes, and fascinating wetlands. The result is an exceptional level of scenic beauty and a rich sense of place. Preserving these resources in the face of ongoing social, economic, and environmental change is one of the key challenges in perpetuating the unique character of the island for future generations.
Photo by Jake Rose
2. North Ferry
Established in 1883 to provide service from Greenport to Shelter Island, the North Ferry is an iconic symbol Shelter island’s history and culture, and it continues to be an essential part of daily life on Shelter Island. During World War 2, the North Ferry transported soldiers, supplies, and equipment to and from the mainland. After the war, the ferry service returned to its role as a vital link between two islands, serving residents, visitors, and businesses alike. Owned by Shelter Island Heights Property Owners Corporation, the North Ferry still provides a dynamic connection between Shelter Island and the North Fork.
Photo by Jake Rose
3. Bridge Street
Bridge Street is the backbone for Shelter Island and its residents. Originally known as Manhasset Avenue, it was the main road that connected Shelter Island to the rest of Long Island. The street was renamed Bridge Street in the late 19th century after a bridge was built over Chase Creek, which runs through the center of the town. In the early 20th century, Bridge Street was Shelter Island’s commercial hub as it became lined with stores, hotels, and restaurants.
During World War 2, Bridge Street was home to a USO center, where soldiers on the island could go for entertainment and relaxation. Today, Bridge Street is still an important part of the community. Many of the historic buildings that once housed hotels and stores now serve as art galleries, restaurants, and boutique shops. The street is also home to the Shelter Island Historical Society, which preserves and shares the history of the town and its residents.
4a. Shelter Island Windmill
Built in Southold in 1810 by Nathaniel Dominy V, the iconic Shelter Island windmill is the only surviving windmill from the North Fork and one of the few left on the East End. Brought into Shelter Island via a barge in 1840, the mill served as the town’s centerpiece for over eight decades. In 1926, Cornelia Horsford moved the mill to Sylvester Manor, where it has presided there to this day. The Windmill Field is the highest natural point on the property and was the first field returned to active agriculture by Sylvester Manor. Today Sylvester Manor is restoring the historic windmill to put it back into operation.
4b. Sylvester Manor
Established in 1651 by Nathaniel Sylvester and his business partners, Sylvester Manor has played a crucial role in the evolving culture of food. During its esteemed history, the Manor was used as a provisioning plantation to grow food for Barbados sugar plantations, a sheep and wheat farm, and a summer home for food scientist and Harvard professor Eben Norton Horsford. In 2008 the Manor was donated by descendants of Nathaniel Sylvester to the nonprofit Sylvester Manor, whose mission is to preserve, cultivate, and share historic Sylvester Manor. Once comprising all of Shelter Island, today the 236-acre Sylvester Manor Educational Farm has become an important part of the Shelter Island community and helped to create a deeper appreciation for the island’s unique cultural heritage through its efforts to promote sustainable agriculture and preserve the island’s history.
5. Shelter Island Country Club
Developed by the Heights Association, the Shelter Island Country Club maintains basically the same design that it had back when it was founded in 1901. Located at the island’s eastern end on the pristine hill known as “Goat Hill” to island residents, the Club is a place where people come together to play golf on Wesley Smith’s sculpted links and enjoy Shelter Island’s natural beauty. In 1902, a new clubhouse was built by Charles Corwin on the site, providing a comfortable space for members to relax and socialize after a round of golf. The club’s historic clubhouse has been restored and modernized, providing a comfortable and welcoming atmosphere for members and guests alike. In 2009, the club was added to the National Register of Historic Places. Today, the Shelter Island Country Club remains a beloved institution on the island, offering a challenging and scenic course for golfers of all skill levels. The course is nine holes and is open to the public.
Photo by Jake Rose
6. Shelter Island History Museum
Open to the public, the museum is a fascinating glimpse of early Shelter Island. In 1761, William’s son, Captain James Havens and his wife, Elizabeth, took over the homestead and named it “Heartsease.” Here, they raised their 11 children. The home was also a store, a tavern, a school, the post office and the town meeting hall which served a community of 27 households. Captain Havens was a privateer during the war for independence and a Representative of Suffolk County in the New York Provincial Congress of 1776. For more information, visit www.shelterislandhistorymuseum.org
Photo by Jake Rose
7. Crescent Beach
Nestled on the northern side of Shelter Island, Crescent Beach beckons visitors with its captivating views and wide sandy beaches. Overlooking Southold and Greenport, this beach provides a scenic backdrop for your beach day. It’s the perfect spot for sunbathing, building sandcastles, or relaxing with a good book. But Crescent Beach isn’t just for relaxation, it’s also an adventure hub where you can kayak and paddleboard to your heart’s content. In the summer, Crescent Beach is a lively community hub, hosting the Independence Day fireworks celebration. So, get ready for a spectacle of colors lighting up the night sky.
Photo from Shelter Island Fireworks
8. Perlman Music Program
Established in 1994 by Toby Perlman and opened in 2000, the Perlman Music Program is the perfect antidote to the isolating environment that young, exceptionally talented classical musicians grapple with while pursuing their craft. This peaceful campus is an excellent refuge for students to escape their demanding lives and come to form a lasting community.
At PMP, their musicians collaborate, support each other, and contribute to camp life. The faculty focuses on their students’ potential to be interesting artists by safeguarding talent and individuality, and encouraging kids to explore, take risks, and develop at their own pace. Today, PMP provides a vibrant curriculum of programs, residencies, concerts, and mentorship. The most promising young musicians from around the world have a platform to thrive, make music together, challenge each other, form life-long bonds, and transform their potential into a life-changing reality.
Photo from Perlman Music Program
12. Taylor’s Island
There’s a piece of hidden history located just off of Shelter Island. On it lies the rustic Smith-Taylor log cabin, which fuses the atmosphere of a beach bungalow with the vibe of an Adirondack cabin. Originally called Cedar Island, Taylor’s Island was bought by Francis Marion Smith in 1899. Smith then built a log cabin in 1900 as a beautiful retreat for his family. In 1939, S. Gregory Taylor bought the title to the island and spruced up the cabin by giving it a bedroom, kitchen, running water, and tower. Today, this seasonal seaside cottage serves as a fabulous reminder for both residents and visitors of the island’s rich history and cultural heritage.
Photo by Darshanbib
20. South Ferry
The South Ferry was established in 1833 by Captain Samuel G. Clark to provide service between his Shelter Island homestead and North Haven using only a rowboat. The first ferry service between Shelter Island to North Haven dates back to before 1716 when cousin and ancestor Jonathan Havens used a sailing sloop. Since 1833, six generations of Clarks (10 including Havens) have run the South Ferry as a safe and reliable way to travel between Shelter Island and North Haven. Today, the South Ferry is an essential part of life on Shelter Island.
Color Shelter Island is filled to the brim with iconic settings such as Bridge Street, Sylvester Manor, Taylor’s Island, Crescent Beach, and the Japanese Bridge, among many others.
Through its 20 beautiful illustrations and detailed descriptions, Color Shelter Island masterfully highlights what makes this gorgeous island so special to its residents and visitors.
