Things to Do on Cuttyhunk Island
Welcome to Cuttyhunk Island, a small but mighty destination packed with natural beauty and unique experiences. Whether you’re here for a day trip or an extended stay, our guide to things to do on Cuttyhunk will help you discover the best activities, from serene beach walks to adventurous fishing excursions. Get ready to experience the quiet charm of Massachusetts’ outermost island.
Explore the Island’s Natural Beauty
Cuttyhunk is a nature lover’s paradise. The island’s landscapes offer stunning views and peaceful retreats. Lace up your hiking boots or simply enjoy a quiet moment by the water.
Hiking & Walking
The best way to see the island is on foot. Take the main road up to Cuttyhunk Lookout Hill for breathtaking 360-degree views of the Elizabeth Islands, Buzzards Bay, and the Atlantic Ocean. It’s an easy, rewarding walk.
Beaches & Swimming
The island’s beaches are perfect for a refreshing dip or a quiet stroll. Here are the primary beaches you can explore:
- Church’s Beach: Located on a secluded, narrow strip of land, this beach is known for its quiet atmosphere. It’s a great spot for peaceful walks and hunting for sea glass.
- Barges Beach: Situated near the ferry dock on the eastern tip of the island, this beach is named for the visible remains of 14 wooden barges buried to stabilize the shore. It’s a popular place for fishing and beachcombing, with views of Martha’s Vineyard.
- Channel Beach: This family-friendly beach has calm, protected waters perfect for swimming and sunbathing. It’s located across the channel from Barges Beach.
Learn more about Cuttyhunk’s beaches and find directions here.
On the Water: Fishing & Boating
Cuttyhunk has a legendary reputation for its fishing, drawing anglers from all over the world. But it’s not just about the big catch—the harbor is a hub of activity.
World-Class Fishing
Cuttyhunk is famous for its striped bass fishing. Join a local fishing charter for a guided trip, or try your hand at surfcasting off the shoreline.
Paddle Sports & Kayaking
Explore the island from the water by kayak or paddleboard. The calm and protected waters of Cuttyhunk Harbor and Cuttyhunk Pond are ideal for a relaxing paddle. These spots offer a great way to enjoy the scenery from a different perspective. If you are bringing your own gear, you can check with the ferry for transportation details.
Historical & Cultural Attractions
Despite its small size, Cuttyhunk is rich in history. Discover the stories of the island’s past, from its early settlement to its modern-day community.
Historical Society & Key Landmarks
Visit The Cuttyhunk Historical Society to learn about the island’s heritage. The beautiful, historic Cuttyhunk Chapel is a central part of the community and a must-see landmark.
The WWII Bunkers on Lookout Hill
At the highest point of the island, Lookout Hill, you’ll find the remains of World War II-era bunkers. These military observation structures were built by the United States Coast Guard in 1941 to watch for enemy U-boats. Today, they are stripped of their equipment and serve as picnic areas, offering a unique historical point of interest and sweeping panoramic views.
Community & Recreation
Cuttyhunk isn’t just about natural beauty; it’s also a vibrant community with great places for recreation and relaxation.
Island Fun & Games
Across from the church, you’ll find a playground for children to enjoy. On your way to the fishing club, you’ll find the pickleball court and a volleyball court, both popular spots for friendly games. These areas are a great way to meet fellow visitors and island residents.
The Cuttyhunk Public Library
For a quiet escape, visit the Cuttyhunk Public Library. It’s located at 19 Tower Hill Road and offers a collection of books, a comfortable reading area, and a place to relax away from the sun. The library is a hub for the community and a perfect stop for any book lover.
Dining & Shopping
You can’t experience Cuttyhunk without tasting the local flavor and finding a unique souvenir to take home.
Local Eateries & Shops
The Lobster Shack and Sopranos Pizza are at the heart of the island’s social scene, while the Ice Cream Shack is a must on warm days.For a full list of all the island’s dining options and shops, check out our comprehensive guide. Discover where to eat and shop on Cuttyhunk Island.
Plan Your Perfect Day
Ready to start planning your visit? Here are a few itinerary ideas to get you started:
- For the Day-Tripper: Arrive on the ferry, grab a coffee at the Cuttyhunk Cafe, hike up Lookout Hill for photos, and then spend the afternoon fishing or relaxing on the beach before heading back. Learn more about the ferry here.
- For the Adventurer: Pack your gear and explore the island on foot. Afterward, reward yourself with some world-class fishing off the shoreline.
- For the Relaxed Traveler: Spend the morning exploring the historic sites, grab a leisurely lunch, and then settle into a peaceful spot on the beach with a good book. Find the perfect accommodations for your stay.
No matter how you choose to spend your time, Cuttyhunk Island offers a one-of-a-kind experience. Use this guide to help you make the most of your trip!