Ready to dip your toes into a refreshing new hobby this summer? If you’re craving adventure, fresh air, and some of the most beautiful scenery in New England, kayaking on the North Shore of Massachusetts is a must-do. With coastal towns like Ipswich, Rockport, Gloucester offering both calm rivers and oceanfront thrills, you’ll find something for every skill level and interest. It’s one of the best places to go kayaking in Massachusetts. Plus, with options accessible by Commuter Rail, it’s the perfect car-free summer adventure!
Paddle Your Way
Calm, Flat-Water Options, Perfect for Beginners: Castle Neck River, Rockport Harbor, Salem Harbor, Plum Island Estuaries
Intermediate Ocean Paddles: Gloucester Harbor, Marblehead
Challenging Ocean Route: Thacher Island
Whether you’re brand new to kayaking or an experienced paddler, there’s a North Shore kayaking experience perfect for you. With views that stretch from salt marshes to open sea, this region offers some of the most unforgettable New England outdoor adventures.
Kayaking on the North Shore: What You’ll See Along the Way
Wildlife:Osprey, seals, porpoises, egrets, great blue herons, and even bald eagles!
Flora & Fauna: Salt marsh grasses, wild roses, beach plum, eelgrass beds, and colorful seaweed.
Historic Sites: Choate Island, Derby Wharf Light Station, Dog Bar Breakwater, Motif #1, Ten Pound Island & Ten Pound Island Lighthouse, Thacher Island Twin Lighthouses
Explore Castle Neck River on the Crane Estate
One of the most scenic spots for kayaking in Massachusetts is Castle Neck River, which winds around the breathtaking Crane Estate in Ipswich. Enter into Crane Wildlife Refuge, which encompasses over 670 acres including Castle Neck River, Choate Island, and Long Island.
This peaceful, flat-water paddle is perfect for beginners. Friendly, expert guides will accompany you, teaching you about the local area as you paddle. Hear about the glacial activity that shaped the area thousands of years ago to the serene salt marsh, osprey nests and the occasional blue heron that occupy the area today. You’ll see Choate Island, a preserved piece of Colonial history that was once a farming community and even a filming location for The Crucible (1996). Wrap up your trip with a visit to nearby Crane Beach for a post-paddle swim and relaxation under the sun.
Pro Tip: You can book this entire experience with Keolis massAdventures! It includes your Commuter Rail train ticket, shuttle service from the station to Crane Estate, kayak rental, guided kayaking tour, and even beach time after kayaking! Reserve your day trip from Boston to kayak Castle Neck River on the Crane Estate today.
Paddle Through Rockport Harbor
Rockport is a postcard-perfect coastal village; kayaking trips from Boston don’t get much better than this! Glide through the peaceful harbor admiring Motif #1, the famous red fishing shack known as “the most painted building in the world”. In true New England fashion, you’ll share the water with sailboats, lobster traps, and maybe even a curious seal or two. Admire the charming town of Rockport the way seafarers would have first seen it: from the sea! This paddle is ideal for beginners or those who want an easy, scenic adventure without any big waves. It’s also a perfect spot to try your hand at stand-up paddleboarding!
After your paddle, you’ll smell the delicious aroma of New England summer beckoning you to grab lunch. Find a nearby restaurant for the freshest, most delicious seafood you’ll find anywhere! We love the fish sandwich from Little Sister Rockport and the lobster rolls at The Fish Shack Bar & Restaurant. Both restaurants are located in the Rockport Harbor area, just a short walk from our favorite kayaking spot. Reserve your guided paddle through Rockport Harbor with Keolis massAdventures for a truly unforgettable summer excursion.
Kayak in Historic Salem
Paddle through Salem’s picturesque harbor and past iconic landmarks like the Custom House and Derby Wharf Light Station. You’ll gain new perspective on the city’s maritime history, spot seabirds and even see the Friendship of Salem tall ship! With calm waters and proximity to downtown, this route is perfect for beginners and history buffs alike.
Complete your day in Salem with delicious food and rich history. Enjoy mouth-watering seafood and stunning waterfront views at the Sea Level Oyster Bar, we’d get the fresh oysters. Or stop into Finz Salem for the crab nachos! Explore the city’s maritime history at the United States’ first National Historic Site: the Salem Maritime National Historic Site. It includes nine acres of land and twelve historic structures along Salem’s waterfront, including the Derby Wharf Light Station.
Explore Plum Island & Parker River National Wildlife Refuge
Launch from Newburyport to explore the calm estuaries around Plum Island and the Parker River National Wildlife Refuge. This area is teeming with wildlife, expect to see snowy egrets, glossy ibises, and even river otters! The water is flat and tranquil, perfect for first-time paddlers, nature lovers and even photographers seeking a quiet paddle. There are no kayak rentals here – you must bring your own to explore these tranquil waters.
Adventure in Gloucester Harbor
Looking for a more thrilling paddle? Head to Gloucester Harbor where you can experience more excitement with light ocean swells, best for intermediate paddlers. You’ll see the historic Dog Bar Breakwater, a massive granite structure built to protect the harbor from storms. Paddle past Eastern Point Lighthouse and the famous Wicked Tuna fishing boats and even explore Ten Pound Island to find some of the best seaglass in Massachusetts. Keep your eyes peeled for porpoises, gulls, and even the occasional sunfish along the way!
Paddle through this coastal New England town’s harbor on the Gloucester Harbor & Annisquam River Kayak Tour with Keolis massAdventures. Along the way you’ll admire the coastline and historic landmarks. If the tides allow, you’ll be able to kayak into the Annisquam River, enjoying tranquil waters and stunning waterfront homes.
Paddle Around Marblehead’s Coastline
Marblehead’s rocky coastline and picturesque harbor make it a dream for kayakers looking for both beautiful views and a bit of a challenge. Launch off Ocean Avenue for access to the harbor. Glide past Marblehead Light Tower (pictured), historic homes and buildings, docked sailboats and Fort Sewall. Seabirds will join you flying overhead and you might even see a seal! The water here can be lively, offering a fun ride for intermediate paddlers.
After your paddle, walk the streets of this historic and quaint New England fishing town. Visit Fort Sewall, whose panoramic views helped to protect the town since its temporary fortification in 1634. Today, it offers a stunning look out into the harbor. You can also visit Chandler Hovey Park, where New England’s only pyramidal skeletal lighthouse still standing, the Marblehead Light Tower. If you love lighthouses, check out our list of The Best Lighthouses in Massachusetts to See This Summer.
Discover Thacher Island and its Twin Lighthouses
For the experienced paddlers, your new favorite adventure awaits! Kayak out to Thacher Island, just off the coast of Rockport for a one-of-a-kind trip. This epic paddle offers stunning ocean views and two historic lighthouses beckoning you towards them. The Thacher Island Twin Lights are the United States’ only active twin lighthouses. They provide navigation to seafarers and a unique and dramatic photo opportunity for everyone else. The adventure doesn’t stop when you set foot on the island: you’re welcome to hike the trails and even climb one of the lighthouses! You may even see seals sunning themselves on rocky outcrops along the way!
This is one of the most visually stunning Boston summer day trips you’ll ever take. Best for those who are up to the physical challenge of kayaking 1.5 miles in ocean swells. You can reserve your seat on this unique kayak & hike adventure with Keolis massAdventures. You trip with Keolis massAdventures includes all necessary kayaking equipment, expert guide, and of course your round-trip transportation from Boston.
Getting There Without a Car
All of these kayaking spots are accessible by Commuter Rail from Boston via the Newburyport/Rockport Line:
- Gloucester Station: for Gloucester Harbor kayaking adventures
- Ipswich Station: for kayaking in Castle Neck River on the Crane Estate
- Newburyport Station: for Plum Island & Parker River Wildlife Refuge
- Rockport (Station: for Rockport Harbor and Thacher Island kayaking trips
- Salem Station: for kayaking in Salem Harbor
- Swampscott Station: for nearby Marblehead access
From each Commuter Rail station, you can order a rideshare service or book with Keolis massAdventures for transportation that will get you to the launch points and on the water quickly! Keolis massAdventures’ convenient adventures bundle your kayaking trip with your train ticket, gear, and of course the transportation from the station! All of our kayaking adventures are led by professional guides and include your kayak rental, life jacket, and of course your paddle!
So what are you waiting for? Invite your friends to dive into one of the most exhilarating things to do this summer in Massachusetts. Grab your ticket today because kayaking on the North Shore is a New England summer must-do, like watching fireworks on the Fourth of July!
