The Best Long Island Road Trip

A drive from the North Fork to the South Fork of Long Island is one of summer’s highlights for us. It’s one of our top East Coast road trips and we don’t have to go far from home to do it. Plus, if you’re short on time, you can do it all in one day.

From Orient Point to Shelter Island, to Montauk and back, this is one trip that lets you see a little of everything the forks have to offer.

We started our trip on a partially sunny Saturday in June. We left the house around 10:30 AM.. This should have been a recipe for disaster. You know exactly what I’m talking about if you’ve ever tried to head out to the North Fork on the weekend. But there was a 30% chance of showers this particular weekend and, as luck would have it, the weather scared most of the traffic away.

Explore the Lavender Fields in East Marion, NY

Leaving from the Shoreham area, we made our way along Sound Avenue. This eventually turns into North Road 48 as it takes you through the best and most beautiful farms and wineries on the North Fork. But the end of June is the perfect time to take in the lavender fields. Our favorite lavender farm is Lavender By The Bay in East Marion. Lavender blooms start mid-June and the different varieties continue to bloom throughout the summer. You can check ahead to see what is in bloom before you go.

You will need to purchase an entry ticket to enter the lavender fields, but the photo-op alone is worth the cost. We also use this time to load up on everything lavender. Some of my favorite are culinary finds. This includes honey from the farm’s beehives, lavender infused sea salt and a generously sized bag of Herbs de Provence.

Lavender by the Bay, East Marion, NY
Lavender by the Bay, East Marion, NY

The temptation to make more stops along the way was fierce, but we were on a mission and continued on to Main Road Route 25. This will take you to the very tip of the North Fork at Orient County Park.

If you need a break at this point, you can pull into the Cross Sound Ferry lot. Here you will find Cross Sound Deli. Their menu has changed recently, but we can assure you, they still carry delicious ice cream. It’s the perfect opportunity to grab a cup or cone of your favorite scoop and take a rest room break.

Once you’ve completed your pit stop, head over to Orient County Park. The park is for fishing access only, so it’s worth bringing your permit and a few poles before going any further. You’ll be rewarded for your effort by some of the most pristine views of the Long Island Sound. From here you can view Plum Island and the Orient Point Lighthouse.

Take the Ferry to Shelter Island, NY and Hike Mashomack Preserve

But don’t stay too long, we still have a full day of adventure ahead. After returning to your car, you’ll want to hop back onto Main Road Route 25 and make your way over to Greenport. This is where you can catch the North Ferry to Shelter Island. It’s important to note that the North Ferry Company only takes cash or check, so make sure to be prepared.

Once across, this is a great time to explore Shelter Island by car and foot. There’s lots of little pull offs along the coastline where you can get out and catch a glimpse of the Peconic Bay. Or take in some of the architecture of the historic and newer homes. If you’re up for a short hike, Shelter Island is home to Mashomack Preserve. Mashomack offers 11 miles of trails that go along the coastline, creeks, woodlands and fields. As with any hiking in the area, be sure to bring tick repellent. Also, stay on trail and avoid the poison ivy. Your efforts are sure to be rewarded.

American Flag Boulder, Shelter Island
Entering Mashomack Preserve on Shelter Island, NY

We chose to take a short trail that started from the parking lot and completed a small loop by some buildings that brought us back to our car again. It was just long enough to explore the area before continuing on our way.

For our next stop, we headed straight for the South Ferry. The South Ferry brings you from Shelter Island to North Haven on the South Fork of Long Island. The South Ferry Company is not the same as the North Ferry Company, but similar payment constraints apply. They’re cash only, so make sure you have your cash handy when you board.

Grab Some Cookies in Wainscott, NY and Drive to Montauk

From here, our goal was to make it out to Montauk, but we had a pit stop in mind. We were headed for Levain Bakery in Wainscott, New York. This is the second retail location of a popular Manhattan bakery and it is AMAZING! The cookies are fresh, gooey, warm and oh so delicious. They’re the perfect compliment to a road trip across the forks.

After trying out our stash of freshly baked cookies, we jumped back into the car and made our way to Montauk. Your best bet is to stay on Montauk Highway Route 27. The best part about this road trip was catching everything after the crowds started to make their way home. We got to Montauk Point State Park around 4:30 PM. It was early enough that we could grab a light snack from the restaurant and use the restrooms while they were still open. The sun had also reached a point in the sky where we weren’t going to be over heated as we made our way down to the coastline.

We spent some time exploring the beach before heading up to explore the grounds around Montauk Lighthouse. If you are looking to explore the lighthouse and museum, and get a passport stamp, be sure to pay attention to their hours. We just missed our opportunity to get up into the lighthouse.

Looking out at Montauk Point State Park
A quick selfie at Montauk Point State Park

After we were done exploring Montauk Point, we jumped back into the car and headed back to South Ferry. We decided to eat dinner on Shelter Island. Our favorite spot to eat is SALT Waterfront Bar and Grill. As we arrived to South Ferry, the sun was just starting to set. By the time we arrived at SALT we were able to get a table overlooking the boats in the marina as the sun lit up the sky behind them. It’s a beautiful experience. If you don’t have kids, you may want to stay a little longer and grab a drink or two at the bar as well.

After dinner, we hopped back into our car once again and made our way to North Ferry. After arriving in Greenport, we started the drive home for a much deserved good night’s rest.

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