Head of the Harbor New YorkATTRACTIONS & THINGS TO DO
Listed below are the best attractions and things to do near Head of the Harbor, New York.
1. Avalon Nature Preserve
SCENIC NATURE RETREAT
Avalon Nature Preserve is a 216-acre oasis featuring woodlands, wetlands, and tranquil trails, offering a peaceful sanctuary for those seeking to immerse themselves in nature. Visitors can wander a network of serene paths, observe diverse wildlife, and discover picturesque meadows and ponds throughout the preserve. The preserve serves as a popular spot for hiking, birdwatching, and quiet reflection amid the beauty of Head of the Harbor.
2. Harmony Vineyards
WATERFRONT WINE TASTING
Harmony Vineyards offers scenic views along the waterfront and a relaxing ambiance for those enjoying award-winning wines. Guests can sample an array of varietals in an elegant tasting room or on the vineyard's picturesque patio overlooking Stony Brook Harbor. The estate blends Long Island's agricultural roots with a sophisticated wine experience just moments from Head of the Harbor's core.
3. Stony Brook Beach
TRANQUIL COASTAL ESCAPE
Stony Brook Beach, located a short drive from Head of the Harbor, is a peaceful spot known for calm waters and scenic sunsets. Families and solo visitors alike enjoy its sandy stretch for sunbathing, swimming, and gentle strolls along the shoreline. Its easy access and relaxed vibe make it a favorite for unwinding in the area.
4. The Atelier at Flowerfield
ARTS AND CULTURE HUB
The Atelier at Flowerfield in nearby Saint James is a vibrant arts center offering workshops, exhibits, and performances year-round. Artistic visitors can explore rotating galleries, engage in hands-on classes, or attend lectures within the creative facility. Its welcoming atmosphere attracts art lovers of all ages from Head of the Harbor and beyond.
5. Setauket-Port Jefferson Greenway Trail
SCENIC CYCLING ROUTE
The Setauket-Port Jefferson Greenway Trail is a three-mile paved path connecting old-growth forests, meadows, and business districts on Long Island's north shore. Cyclists and walkers enjoy the trail's gentle terrain and lush landscapes, which are accessible to all skill levels. It's ideal for those seeking a leisurely ride or walk near Head of the Harbor.
6. Old Field Point Lighthouse
HISTORIC BEACON VIEWS
Old Field Point Lighthouse is a historic landmark perched at the northern tip of Old Field, just minutes from Head of the Harbor. This iconic beacon, dating back to 1823, rewards visitors with sweeping views of Long Island Sound and fascinating glimpses into maritime history. The lighthouse is a favorite for photographers and history enthusiasts alike.
7. Long Island Museum
REGIONAL HISTORY SHOWCASE
The Long Island Museum offers engaging exhibits focused on art, history, and American culture, located in nearby Stony Brook. Guests can explore galleries featuring carriages, regional artwork, and rotating special collections. Its immersive displays provide meaningful insight into the area's heritage for visitors from Head of the Harbor.
8. Stony Brook Village Center
CHARMING SHOPPING DISTRICT
Stony Brook Village Center is an inviting, colonial-style hub with boutique shops, galleries, and eateries just south of Head of the Harbor. The walkable square hosts seasonal events and offers a delightful atmosphere for browsing unique gifts or enjoying local delicacies. Its picturesque setting by the harbor draws both locals and visitors alike.
9. Sunken Meadow State Park
BEACH AND WILDLIFE HAVEN
Sunken Meadow State Park is a beloved recreation area with sandy beaches, tidal marshes, and wooded trails on the Nissequogue River, easily accessed from Head of the Harbor. Visitors can swim, picnic, launch kayaks, or watch wildlife, all with panoramic water views. Its extensive facilities make it a perfect destination for outdoor enthusiasts.
10. Long Island Greenbelt Trail
EPIC HIKING ADVENTURE
The Long Island Greenbelt Trail offers miles of hiking through serene woodlands, meadows, and wetlands, with parts running close to Head of the Harbor. Hikers are treated to diverse wildlife, beautiful overlooks, and peaceful natural settings. The section near Sunken Meadow Creek is particularly celebrated for its stunning views.
11. Shopping
BOUTIQUES AND LOCAL FINDS

Shopping in and around Head of the Harbor delights visitors with a blend of quaint boutiques, artisan shops, and specialty retailers. Stony Brook Village Center stands out with its charming stores, while Chocolate Works offers sweet treats and gifts. With local options for fashion, crafts, and gourmet goodies, shopping here is a personalized experience.
12. Dining
CULINARY EXPERIENCES APLENTY

Dining near Head of the Harbor features a diverse array of restaurants catering to every palate. Favorites include The Three Village Inn for classic American fare, Pentimento for Italian cuisine, and Sweet Mama's for homestyle comfort food. Visitors can enjoy waterfront views, cozy atmospheres, and delicious local ingredients at these popular establishments.
13. Hiking
NATURE TRAIL ADVENTURES

Hiking options in Head of the Harbor are plentiful and scenic, highlighted by trails at Avalon Nature Preserve and segments of the Long Island Greenbelt Trail. These routes traverse woodlands, open fields, and picturesque wetlands, offering something for every experience level. Nature enthusiasts appreciate the tranquility and wildlife encountered throughout these hiking destinations.
14. Fishing
WATERSIDE ANGLING SPOTS

Fishing opportunities abound in the Head of the Harbor area, particularly along Stony Brook Harbor and the adjacent Nissequogue River. Anglers can cast lines from local docks, embark on charter excursions, or enjoy peaceful shoreline fishing for species like striped bass and bluefish. The area's blend of calm waters and natural beauty makes it a favorite for both casual and dedicated fishers.
15. Camping
OUTDOOR OVERNIGHT ESCAPES

Camping near Head of the Harbor is best enjoyed at Sunken Meadow State Park, which offers designated camping areas along with beach access and hiking trails. Campers can set up beneath shady trees and savor evenings by the water, taking advantage of park amenities and scenic surroundings. It's an ideal base for exploring the natural wonders of Long Island's North Shore.