Smithtown on Long Island offers diverse outdoor fun with hiking trails, kayaking on the Nissequogue River, and quiet biking routes. Ideal spring through fall, it’s a great spot for nature lovers seeking peaceful parks and waterfront adventures.
Smithtown on Long Island offers diverse outdoor fun with hiking trails, kayaking on the Nissequogue River, and quiet biking routes. Ideal spring through fall, it’s a great spot for nature lovers seeking peaceful parks and waterfront adventures.
Outdoor Activities in Smithtown, New York
Smithtown is a charming town on Long Island known for its natural beauty and outdoor opportunities. Whether you enjoy hiking through forest preserves, paddling calm rivers, or cycling peaceful country roads, Smithtown offers a variety of activities to connect with nature.
Discover the unique natural wonders, summits, and scenic landmarks that make Smithtown, New York special.
★ 7.8⌖ 5.49 milesEasyExplore the Stony Brook Reservation in Boston with its network of easy trails perfect for hiking and birdwatching. Enjoy a peaceful environment and historic features like stone bridges, all within easy reach from the city.
★ 7.8⌖ 24.23 milesExplore the tidal island of Charles Island near Milford, CT, accessible by a tombolo during low tide. Known for birdwatching and historical lore, it offers unique views and a quiet retreat for nature lovers.
★ 7.8⌖ 24.45 milesExplore the Mianus River in Greenwich, CT, a serene spot for fishing, hiking, and birdwatching. It offers easy access and vibrant ecological diversity, perfect for a peaceful day in nature.
★ 7.5⌖ 24.49 milesExplore fly fishing at Housatonic River in The Berkshires. Known for its trout-filled waters and serene environment, it's an ideal spot for both seasoned anglers and newcomers. Best visited in spring or fall with drive-in access. Don't forget your fishing gear.
★ 7.8⌖ 29.18 milesExplore the Housatonic River in Connecticut, perfect for canoeing and kayaking. Enjoy hiking trails that offer stunning river views and fly fishing opportunities in Cornwall. Accessible from U.S. Route 7, this serene spot is best visited in spring and fall.
★ 5.5⌖ 30.98 milesExplore Weir Farm National Historical Park in Wilton, CT. This unique landmark combines art with nature and is perfect for art enthusiasts and families. Enjoy hiking, painting workshops, and self-guided tours. Best visited in spring and fall for vibrant scenery.
★ 7.5⌖ 35.56 milesExplore the charming Thimble Islands off Branford, CT. Ideal for kayaking and wildlife watching, these islands offer tidal views and historical allure. Access by boat only; best visited in spring or fall for a serene experience.
★ 8.5⌖ 35.73 milesModerateExplore the moderate-difficulty trails of West Rock Ridge State Park near New Haven, CT. Ideal for adventure seekers, enjoy hiking with stunning vistas and historical sites like Judges Cave. Best visited in spring or fall for colorful scenery and quieter trails.
★ 7.8⌖ 35.97 milesExplore East Rock Park in New Haven, CT. Known for hiking and biking, the park offers varied trails and stunning city views from a 366 ft ridge. Enjoy bird watching by the Mill River. Best visited in spring and fall.
★ 7.8⌖ 36.47 milesExplore Lake Zoar in Connecticut, a serene spot for kayaking, fishing, and hiking. The quiet landscape offers scenic views, making it family-friendly. Popular for birding, visitors can enjoy observing local wildlife. Accessible by car, it's best visited in late spring to early fall.
★ 7.8⌖ 37.49 milesEasyExplore Tarrytown Lakes Park in Tarrytown, NY, featuring easy lakeside trails perfect for hiking and wildlife viewing. Appreciate peaceful fishing spots and enjoy beautiful autumn foliage. Suitable for families and nature lovers year-round.
★ 4⌖ 38.63 milesDiscover Tarrywile Park in Danbury, CT, with its scenic trails, historic Hearthstone Castle, and Tarrywile Mansion. Enjoy hiking, birdwatching, and picnicking in a tranquil setting. Best visited in spring or fall.
Discover the top adventure activities and curated experiences in Smithtown, New York, verified by our editors to help you make the most of your trip.
Book unforgettable outdoor adventures, guided tours, and gear rentals with verified Local Experts in Smithtown, New York.
⌖ 5.5 miA concise guide to the operator, gear options and what to expect during a 2‑hour rental from Long Island Canoe & Kayak Rentals.
⌖ 8.2 miA 1- or 2-hour sightseeing cruise from Oakdale that visits the lighthouse, Robert Moses Beach and the Atlantic—customizable for private groups of up to 10.
⌖ 9.0 miA guided, one-hour kayak outing on the Connetquot River that pairs on‑land instruction with calm paddling past waterfront homes and regular wildlife sightings.
⌖ 9.3 miA two-hour guided kayak tour that crosses the Connetquot River and winds through Oakdale’s canals, pairing calm paddling with on‑land instruction and interpretive commentary.
⌖ 9.4 miA narrated sail aboard the restored oyster boat Priscilla, departing from the Snapper Inn, that moves from the Connetquot River into the Great South Bay and lets riders participate in raising the sails.
An evening sailing experience operated by the Long Island Maritime Museum; note that guests are advised to grab dinner either before or after their sail.
New for 2026, this sunset cruise operated by the Long Island Maritime Museum runs on either the bay or the river at the captain’s discretion — this guide explains what to expect from that simple, evening outing.
⌖ 11.6 miA guided public food tour that visits roughly five off‑the‑tourist eateries on Manhattan’s west side, useful for travelers who want practical restaurant recommendations and an authentic, wallet‑friendly New York meal experience.
⌖ 11.6 miA seasonal, end-of-year food tour that takes you beyond Midtown tourist traps to five permanent Midtown stops — including at least one sweet stop — traveling like a New Yorker by subway and on foot.
⌖ 11.7 miOne-hour guided rafting on the Upper Deschutes with transportation from Bend — a compact whitewater run that mixes mellow swimming holes and class 3 rapids for ages 6 and up.
⌖ 12.6 miA 10-minute parasailing flight over Fire Island operated from Ocean Bay Park — this guide explains the logistics, durations, and what to bring for the trip.
⌖ 14.1 miA three-hour, instructor-led sea‑kayak outing that pairs easy paddling with shoreline views of Cold Spring Harbor Laboratory, notable historic homes and coastal landmarks.
⌖ 14.4 miA one-hour tubing trip on the Great South Bay near Ocean Beach — tubes hold up to four riders and the boat carries up to ten guests.
⌖ 14.4 miA concise guide to the Cherry Grove parasail that outlines the 10‑minute flight, boat time and what to bring so you can plan a seamless outing on Fire Island.
⌖ 14.4 miAn hour or two of close-to-shore tubing for groups — this guide lays out logistics, capacity, and what to bring for a safe, sun-forward outing.
Make the most of your visit to Smithtown, New York with these essential planning tips, seasonal events, and protected lands.
Smithtown, New York hosts celebrated events throughout the year showcasing the region's culture, outdoor lifestyle, and community spirit.
Experience the vibrancy and unique outdoor heritage of Smithtown, New York during the iconic Smithtown Boat Show & Family Fun Day. Plan accommodations and permits early.
Experience the vibrancy and unique outdoor heritage of Smithtown, New York during the iconic Caleb Smith State Park Spring Trail Day. Plan accommodations and permits early.
Experience the vibrancy and unique outdoor heritage of Smithtown, New York during the iconic Nissequogue River Paddlefest. Plan accommodations and permits early.
Smithtown, New York is surrounded by incredible protected natural lands offering pristine trails, wildlife habitats, and wilderness conservation.
Sleeping Giant State Park in Connecticut features a series of rugged hiking trails over a prominent traprock mountain ridge, offering spectacular views and a unique natural landscape.
Harriman State Park, located in New York, offers a vast terrain of forested hills and valleys, making it a prime spot for outdoor enthusiasts seeking hiking, camping, and wildlife observation.
Ramapo Mountain State Forest offers a diverse range of outdoor activities, from hiking to fishing, amidst the serene landscape of northeastern New Jersey.
Enders State Forest in Connecticut offers vibrant natural beauty with lush forests, scenic waterfalls, and varied recreational opportunities for outdoor enthusiasts.
Bring insect repellent when hiking or paddling in warmer months.
Weekdays tend to be less crowded at popular parks and launch sites.
Check tide schedules before kayaking in coastal areas.
Wear sunscreen and stay hydrated during summer outdoor activities.
Always check local regulations, fire restrictions, trail conditions, and weather forecasts before setting out on any adventure in Smithtown, New York. Respect nature, wildlife, and fellow adventurers by following Leave No Trace principles.