Summer on Shelter Island is everything it should be: slow mornings, sun-warmed afternoons, and soft, salty nights by the water. Whether you’re in town for a weekend breather or settling in for a full retreat, this peaceful island gives you space to unwind without needing to go far.
With tucked-away beaches, tree-lined trails, and quiet harbors, Shelter Island, NY, blends calm with a sense of discovery. The beautiful waterfront pulls you in: kayaks slipping through the inlets, sailboats drifting near the shore, and sunsets casting long shadows in orange and lavender. If you’re staying at The Rams Head Inn, you’re already right where you need to be.
Top Things to Do on Shelter Island This Summer
Wondering what to do this summer on Shelter Island? These guest favorites mix outdoor fun with coastal simplicity:
- Kayaking: Paddle through hidden inlets and calm creeks right from our private dock.
- Paddleboarding: Test your balance and take in wide-open harbor views on a SUP board.
- Sailing: Charter a boat or cruise the bay under your own sail.
- Swimming: Dip into Rams Head Cove or stretch out on the beach with your toes in the sand.
- Hiking: Wander the trails at Mashomack Preserve and spot native birds along the way.
- Pickleball: Rally with friends or family with a lively game of pickleball on our sunny courts.
Couples enjoy quiet walks or hammock chats, families love lawn games and beach swims, and solo guests get space to breathe.
A Perfect Summer Day on the Waterfront
Looking for the perfect summer flow? Here’s an itinerary that takes you through a full day at Rams Head:
Morning
Ease into the day with coffee by Coecles Harbor. Then set off on a kayak ride or a light paddleboard loop. Early mornings mean calmer water and fewer crowds.
Afternoon
After drying off, grab a garden lunch and lounge in the shade. You might read, nap in a hammock, or play a round of pickleball. Nothing’s rushed here.
Evening
As golden hour sets in, enjoy drinks on the beach or under the gazebo, and tuck into a seafood dinner. Stay for the music, the board games, or just the hush of the harbor as the sky fades to navy.
Is Shelter Island Worth Visiting in Summer?
Absolutely. If your idea of summer includes paddleboards, sunsets, and long, quiet evenings, Shelter Island belongs on your list. It has the kind of gentle pace that lets you breathe deeper and sleep better.
Though it feels far from the city, it’s actually just a short ferry ride from Long Island’s North or South Fork. You’ll go from busy streets to a private waterfront in just a few hours.
Easy Family Fun in a Peaceful Setting
Shelter Island’s pace suits families perfectly. Play hula hoop on the lawn, swim as a group, or pull out a board game when the sun dips. You can be active or take it slow. There’s no right or wrong way to spend your time.
Waterfront Dining With Seasonal Flavors
Dinner at Rams Head isn’t just a meal: it’s an experience. Whether you dine in the gazebo or settle in by the water, our dishes use local seafood, garden herbs, and seasonal produce. From roasted oysters to garden cocktails, each plate connects you to the island.
Getting Here Is Easier Than You Think
Hop on a ferry from Greenport or North Haven. If you’re coming from the city, take the train to the East End, then cross the water. Boaters can dock with help from Captain Dave. Reach out on Channel 77 for mooring assistance.
Plan Your Shelter Island Summer Getaway
Water activities at The Rams Head Inn typically run from May through October, but summer is when the island is truly in its prime. Before you visit, be sure to:
- Check ferry schedules and the local weather forecast
- Call ahead for waterfront dining or chartered boat experiences
- Bring swimwear, sneakers, and something breezy for sunset cocktails
Ready for the perfect mix of activity and ease? Shelter Island and The Rams Head Inn are here to make it happen. Book now or check availability to plan your stay.
