Some of the East End’s most memorable moments don’t happen on land, they happen on the water.
Paddle through quiet salt marshes as ospreys soar overhead, glide across a glassy bay at sunrise, or catch your first wave at Ditch Plains. From the protected waters of the Peconic Estuary to the Atlantic surf of Montauk, Long Island’s East End offers countless ways to experience the shoreline beyond the beach.
Whether you’re looking for an active outdoor adventure or simply a relaxing afternoon on the water, there’s an experience waiting for every pace and every skill level.
Did You Know?
The Peconic Estuary stretches between the North and South Forks and includes more than 100 distinct bays, harbors, and tributaries, creating one of New York’s most diverse environments for kayaking, paddleboarding and wildlife viewing.
Choose Your Adventure
Whether you’re looking to paddle or catch your first wave, the East End offers something for everyone.
Kayaking
Explore peaceful rivers, winding creeks, and protected estuaries surrounded by wildlife.
Stand-Up Paddleboarding
Glide across calm bays and harbors while taking in a completely different perspective of the shoreline.
Surfing
Ride Atlantic waves or take your first lesson at one of Long Island’s most iconic surf destinations.
Kayaking
The protected waters of the Peconic Estuary make the East End one of Long Island’s most enjoyable places to explore by kayak. Calm rivers, quiet creeks, and scenic marshes create an ideal setting for beginners, families, and experienced paddlers alike.
Peconic River | Riverhead
One of the more popular launching points on the East End, the Peconic River winds through wetlands rich with birds and native wildlife before gradually opening toward Flanders Bay. The calm current makes it an excellent choice for first-time paddlers and families.
Coecles Harbor | Shelter Island
This protected marine water trail offers peaceful paddling through one of the East End’s most naturally preserved environments. Along the way you’ll discover quiet coves, salt marshes, and abundant wildlife.
Orient Beach State Park
Located at the eastern tip of the North Fork, Orient Beach State Park provides easy access to the calm waters of Gardiners Bay and Peconic Bay, making it another excellent destination for exploring by kayak.
Outfitters & Rentals
Riverhead – Long Island Canoe Kayak Rentals and Peconic Paddler both rent kayaks and canoes right on the Peconic River, so you can launch a few steps from the dock and drift past marshes, ospreys, and riverfront views at your own pace.
Shelter Island – Kayak Shelter Island runs guided tours and self-guided rentals on Coecles Harbor, launching right onto the protected marine water trail above; reservations are required, so text ahead rather than count on walking up.
Orient Beach – Eagle’s Neck Paddling Company, on Hallock’s Bay inside Orient Beach State Park, adds kayak and paddleboard rentals close to Gardiners Bay and the tip of the North Fork, opening up quiet coves and open water.
Local Tip
Plan your paddle into the wind on the way out so the return trip is easier when you’re heading back to shore.
Stand-Up Paddleboarding
Stand-up paddleboarding has become one of the East End’s favorite summer activities thanks to its calm bays and protected harbors. Early mornings often bring mirror-like water that’s perfect for beginners and experienced paddlers alike.
Gull Pond | Greenport
Just off Greenport Harbor on the North Fork, Gull Pond (also known as Norman E. Klipp Park) is a small, sheltered tidal pond that is calm, scenic, and forgiving for beginners.
Crescent Beach | Shelter Island
On Shelter Island’s west shore, Crescent Beach (also called Sunset Beach) is a calm, Sound-facing stretch that’s ideal for an easy paddle especially at golden hour, when it earns its nickname.
Mecox Bay | Southampton
Calm summer conditions make this an inviting location for those looking for a leisurely paddle.
Northwest Creek | East Hampton
Protected water and scenic marshes create one of the area’s most peaceful paddling experiences.
Lake Montauk
One of Montauk’s largest bodies of water offers plenty of room to explore while enjoying views of the surrounding coastline.
Outfitters & Lessons
Greenport – One Love Beach rents boards and hosts a free weekly community paddle exploring the coves and estuaries around the harbor.
Shelter Island – Venture Out sets up on Crescent Beach and delivers boards free anywhere on the island, easy for a glassy morning or a sunset paddle.
Southampton – Adventure Paddleboards & Kayaks, based in Hampton Bays, offers family SUP and kayak rentals and lessons. Mecox Bay itself has no on-site rental, it’s bring-your-own, with permit or day-pass parking at Scott Cameron Beach, so plan to rent nearby and cartop your board in.
East Hampton – Paddle Diva focuses on stand-up paddleboarding in the sheltered water around Three Mile Harbor, ideal for glassy, low-traffic early mornings.
Montauk – Sunset Surf Shack and The H2O Generation both rent boards and deliver anywhere in town, including Lake Montauk launches. (Adventure Paddleboards also runs a Fort Pond location.)
Local Tip
Always check the wind forecast before heading out. Conditions can change quickly, even on sunny summer days.
Surfing
Few places are as closely connected to East Coast surfing as Montauk.
Summer brings smaller, more beginner-friendly waves, while the larger swells of fall attract experienced surfers from around the region.
Cupsogue Beach | Westhampton
At the western edge of the East End’s surf beaches, Cupsogue Beach County Park sits where Moriches Inlet meets the Atlantic, a dependable beach break and a quieter, less-crowded alternative to Montauk. As a county park, it’s also one of the easier ocean beaches for non-residents to reach on a day pass.
Amagansett
Less crowded than Montauk, Amagansett offers another excellent option for beginners looking to learn.
Ditch Plains | Montauk
Perhaps the East End’s most recognizable surf beach, Ditch Plains welcomes everyone from first-time surfers to seasoned locals.
Surf Lessons & Rentals
Westhampton – Island Surf, a village fixture since 1998, rents surfboards and paddleboards by the day or week and offers private lessons, the go-to shop for the western end near Cupsogue.
Amagansett – There’s no surf school on the beach here, which keeps it the quieter, more local alternative. Most visitors book a lesson or grab a rental board in Montauk, a short drive east, and paddle out on their own.
Montauk (Ditch Plains) – East End Surf Club and CoreysWave both run private and small-group lessons right at Ditch Plains, for first-timers through intermediates. For gear, Air + Speed in town rents surfboards and wetsuits by the day.
Local Tip
Parking near popular surf breaks can be limited during the summer months, so check local parking regulations before heading out.
Make a Day of It or an Overnight
The East End rewards a full day on the water but the region really opens up when you stay the night. Trading the drive home for a sunset dinner, a quiet morning harbor, and a second day to explore is what turns a good outing into a true getaway.
Riverhead
Launch a kayak on the Peconic River, enjoy lunch in downtown Riverhead, then spend the afternoon exploring local attractions and farm stands. Stay the night and you can start the next morning on the riverfront before heading east into wine country.
North Fork
Start the day paddling along the shoreline before visiting nearby wineries, roadside farm stands, and waterfront restaurants. Book a room at a North Fork inn or waterfront hotel, and a single afternoon becomes a relaxed weekend of vineyards, sunsets, and slow mornings by the bay.
Shelter Island
Explore Coecles Harbor by kayak, enjoy lunch overlooking the water, then catch the ferry back to Greenport or Sag Harbor or stay and let the island work its quiet magic, with an overnight at a historic inn and a morning paddle before the day-trippers arrive.
Montauk
Begin with a morning surf lesson, explore Montauk’s shops and restaurants, and finish the day watching the sunset from Montauk Point. Make it an overnight at one of Montauk’s oceanfront hotels or motels, and you’ll be first in the water when the waves roll in at dawn.
Make It an Overnight
Whichever corner of the East End you explore, there’s a place to wake up nearby and a night here is what makes the trip worth extending. Explore where to stay across the East End →
Before You Go
- Reserve rentals and lessons in advance during the summer season.
- Check wind and weather conditions before heading out.
- Confirm parking and launch access before your trip, particularly in East Hampton and Montauk.
- Wear appropriate footwear and sun protection.
- If you’re new to paddling, begin in the protected bays and rivers before venturing into larger bodies of water.
Experience the East End from the Water
However you spend it: a first wave or a slow morning paddle, a day on the East End’s water has a way of pulling you back. Slow down, breathe in the salt air, and let the shoreline you came to see become the reason you return.