Our Shelter Island Weekend Getaway

Best Breakfast Spots on Shelter Island

Best Beaches on Shelter Island

Best Things to Do on Shelter Island

Shelter Island is located between Greenport on Long Island’s North Fork and North Haven, just outside Sag Harbor on the South Fork. Because there is no bridge connecting the island to the rest of Long Island, every visit begins with a ferry ride.

There are two main ways to reach Shelter Island:

• From the North Fork (our preferred route): Drive to Greenport and take the North Ferry, which arrives in Shelter Island Heights. This is the route we took and a convenient option when traveling through Riverhead, Southold or Greenport.

• From the South Fork: Travel through Sag Harbor to North Haven and take the South Ferry to the southern end of Shelter Island.

The North and South ferries are operated by separate companies, so schedules, fares and payment options may differ. We usually take the North Ferry and they take cash only. Both ferries transport vehicles, bicycles and walk-on passengers. Reservations are generally not required, and vehicles board on a first-come, first-served basis.

You can also take the Long Island Railroad to Greenport and walk to the North Ferry terminal. The Greenport station lists the North Ferry as a nearby connection to Shelter Island. However, bringing a car is the easiest option for a weekend visit, especially if you plan to explore the island’s beaches, town landings, nature trails and restaurants.



As soon as we drove off the ferry and into Shelter Island, you feel a wave of relaxation. The humming noise of highways and the whoosh of traffic all is left behind you in Greenport. I always feel like I am transported into a place where time slows down.

We had a busy first day planned, beginning with one important stop before breakfast: Shelter Island Town Hall to pick up our beach parking pass!

Before heading to breakfast or exploring the island, our first stop early Saturday morning was the Shelter Island Town Hall. During the summer season, a parking permit is required at many of the island’s public beaches, town landings and waterfront access points. Having a parking pass gave us the freedom to explore different areas of the island throughout our stay without having to worry about where we could legally park.

Even though we were only going to be on Shelter Island for four days, I opted for the Weekly Beach Parking Pass to give us this freedom to explore over the daily pass which is only valid at the specific beach or landing you choose.

The Town Clerk’s Office is located at 38 North Ferry Road, only a short drive from the North Ferry. Summer Saturday hours are limited to 8:00 a.m. to 10:00 a.m., so this is one stop you will want to plan ahead for, especially if you arrive on the island for a weekend getaway.

Beach parking permits are required from May 15 through September 15. The permit applies to designated parking areas at popular locations such as Wade’s Beach, Shell Beach, Crescent Beach on weekends, Menhaden Lane, Fresh Pond and several smaller town landings.

Helpful tip: Bring your vehicle registration and proof of where you are staying on Shelter Island when purchasing a nonresident weekly or longer-term pass. Cash is preferred when paying at town hall, but they do accept credit card with an add-on processing fee, which I feel is normal for most businesses.

One-day parking passes can also be purchased through the ParkMobile app, but since we planned to visit several beaches and landings during our extended weekend, stopping at Town Hall first made the rest of our trip much easier.

Once our beach pass was taken care of, we were ready for the next important part of our Saturday morning: breakfast!

After picking up our beach parking pass, we headed to The Islander for breakfast. It was a convenient stop to start the morning, with a menu full of familiar breakfast favorites and a few more creative options.

Pete ordered the Crab Cake Eggs Benedict and I had the Tex-Mex Omelette. Both meals came with home fries, toast and coffee, making it a filling breakfast before a busy day of exploring the island.

While the food was not our favorite breakfast of the weekend, the portions were generous and there were plenty of choices on the menu. The coffee was also not quite what we were looking for, and since sitting down with a really good cup of coffee is one of our favorite parts of vacation mornings, we decided to try a few other breakfast spots during the rest of our stay.

The Islander may still be a good option for visitors looking for a casual, family-friendly, traditional sit-down breakfast with a broad menu and hearty portions.

Since we still had a few hours before checking in at Shelter Island House, we used the rest of our Saturday morning to explore a few local spots. One of the best things about Shelter Island is that you do not need an overly complicated itinerary. A farmers market, a quirky antique shop and a quiet walk along the water can easily fill an enjoyable morning.

Havens Farmers’ Market

Our next stop was the Havens Farmers’ Market, held on the grounds of the Shelter Island History Museum. During the 2026 season, the market runs every Saturday from May 23 through September 5, from 9:00 a.m. to 12:30 p.m.

The market is a wonderful way to experience the local side of Shelter Island. Vendors offer a little bit of everything, including seasonal produce, fresh fish, artisan cheeses, baked breads, pies, pickles, desserts and other locally made foods. You will also find flowers, handcrafted goods, jewelry, artwork and tables featuring businesses and organizations from around the Island.

Be sure to walk through the entire market rather than stopping at the first few tents. Toward the back of the grounds, we found musicians playing folk music, which added to the relaxed, community atmosphere. It was the kind of place where you could browse for a few minutes or spend the entire morning slowly making your way from one vendor to the next.

Browsing Marika’s Eclectic Boutique

After the farmers market, we took the short drive to Marika’s Eclectic Boutique. Stepping inside feels a little like entering a treasure hunt, with an interesting collection of vintage furnishings, lighting, décor and unexpected items from decades past. The shop is especially known for its vintage and mid-century furniture and one-of-a-kind pieces.

We took our time looking through the curiosities tucked throughout the shop. There were vinyl records, 8-track tapes and even CDs—the types of things that once felt completely ordinary but have now become small reminders of another time.

You never quite know what you might uncover here. Even when you are not shopping for something specific, it is an interesting place to browse. For anyone decorating a home or looking for a vintage piece that cannot be found in a typical furniture store, Marika’s is worth adding to your Shelter Island itinerary.

A Walk to Kissing Rock

Knowing that we still had some time before check-in, we hopped back into the car and followed Shore Road toward Rocky Point Road and made our way to Kissing Rock. You will know you have arrived when you see the enormous boulder painted with an American flag at the water’s edge.

Kissing Rock is one of my favorite places to visit on the first day of a Shelter Island getaway. It is not a large, traditional beach with facilities or crowds. Instead, it is a quiet place to walk beside the water, listen to the lapping calm waters, look for shells and begin settling into the slower pace of the Island.

We arrived during low tide, which gave us more shoreline to explore. We first walked as far as we could to the left of the rock and then headed in the opposite direction until we reached the first set of jetty rocks. Along the way, we found tiny seashells scattered across the sand and stopped to watch the activity on the water.

There are also osprey nests visible from the shoreline, so keep an eye on the sky. You may catch sight of an osprey circling above the water or diving down in search of a fish.

Kissing Rock has been a well-known local meeting place for generations. According to the Shelter Island Historical Society, its romantic nickname dates back to before the surrounding area was developed, when couples came to the secluded waterfront to enjoy the moon, stars and privacy.

After our walk, it was finally time to head to Shelter Island House, check in and officially begin our extended weekend.

After our walk along the shoreline at Kissing Rock, we headed to Shelter Island House to see whether we could check in. The boutique hotel is located at 11 Stearns Point Road in Shelter Island Heights, just a short distance from Crescent Beach and many of the places we planned to visit throughout the weekend. The property features a seasonal outdoor pool, complimentary bicycles, Wi-Fi and beach essentials such as chairs, umbrellas and towels.

Our scheduled check-in time was 3:00 p.m., but when we arrived at the front desk at around 12:30 p.m., we were pleasantly surprised to learn that our room was already prepared for us.

No matter where we travel, it is always a great feeling to get into the room early, unpack and settle in. Once the bags are put away and everything is organized, that is when vacation officially begins for us!

We were greeted by the loveliest and most helpful front desk attendant. She walked us through the hotel’s amenities and told us about some of the local events taking place during our stay. Since the Shelter Island Fireworks were happening that evening, she recommended walking down Shore Road at around 8:50 p.m. to find a place to watch the show.

Our Room at Shelter Island House

We brought our luggage to the room and began unpacking. The room had plenty of storage for our clothing and belongings (a large dresser and armoire and two nightstands), which made it easy to get organized for our extended weekend.

The only area that could have benefited from a few additional practical touches was the bathroom. An extra shelf, a few hooks and another towel bar would have been helpful, particularly when getting ready in the morning. There was not much counter space for toiletries or makeup, and the lighting in the main room was not ideal for getting ready.

This certainly did not take away from our stay, but it is something to keep in mind when packing. A hanging toiletry organizer or small travel mirror could be helpful if you like having all your items easily accessible.

After unpacking, we checked the ice in our cooler to make sure everything was still cold. We were all set, but Shelter Island IGA is a convenient stop if you need ice, drinks, snacks or any other last-minute supplies during your stay.

With everything taken care of, we spent part of the afternoon relaxing near the pool under the large pavilion in the backyard. After a busy morning of ferry rides, shopping and walking along the beach, it felt good to slow down and enjoy the property before dinner.

For our first dinner on the Island, we made reservations at Blue Han, the Korean kitchen and café located inside Shelter Island House.

Blue Han describes its concept as a meeting of Korean tradition and the calm rhythm of Island life. The restaurant serves thoughtfully prepared Korean dishes in a comfortable setting that feels refined without being overly formal. Guests can sit inside, at the bar or outside on the hotel’s front porch.

The restaurant was completely full and very busy on the Saturday evening we visited, so reservations are a good idea during a summer weekend.

We each ordered one of the restaurant’s Signature Trays. We tried the Spicy Korean Chicken Tray and the Korean Spicy Pork Tray, also known as Jeyuk Bokkeum. The trays were generously portioned and included plenty of food to create a satisfying, complete meal.

Everything was fresh and made to order. By the time we finished, we were both so full that we decided to skip dessert—which does not happen very often while we are on vacation!

Blue Han’s schedule may vary throughout the week and season. During our visit, it was closed Monday and Tuesday evenings. I recommend checking the restaurant’s online reservation system or calling before making plans. Pickup ordering is also available, which could be a convenient option if you would rather enjoy dinner by the pool or take it to a nearby waterfront spot.

After dinner, we returned to our room for a little while before walking down toward Shore Road for the 67th Annual Shelter Island Fireworks.

The show took place over Crescent Beach on Saturday, July 11, 2026. This annual display is organized by a nonprofit community organization and supported through donations, fundraising events and the generosity of local residents and businesses.

The weather could not have been better. The night was clear and comfortable, and people gathered along the shoreline to find their own viewing spots. There was a wonderful sense of community as residents, visitors and local businesses came together to enjoy one of Shelter Island’s favorite summer traditions.

Since 2026 marked the 250th anniversary of the signing of the Declaration of Independence, the display felt especially celebratory.  The show seemed a little longer and grander than usual, with beautiful bursts filling the sky and reflecting across the water.

And, of course, there were the smiley-face fireworks—one of those small, playful details that made everyone along the shoreline cheer.



Watching fireworks over the water was the perfect way to end our first day on Shelter Island.

The rest of our extended weekend was spent doing what we enjoy most on Shelter Island: exploring.

Even though we have been visiting almost every summer since 2013, we continue to discover new places while returning to old favorites. There is always another quiet beach, small shop, breakfast spot or waterfront road to experience.

We also try to support as many local businesses as possible during each visit. Below are links to the rest of our series to read more about our favorite beaches, breakfast stops, shops and things to do from this year’s Shelter Island getaway.