Day Trip to Long Island, New York from New London, Connecticut

I’ve lived in southeastern Connecticut my entire life and somehow, I’ve never taken the ferry to Long Island. It’s not like I’ve never taken a ferry out of New London before. I’ve taken the Block Island Express for a Block Island day trip, I’ve taken the ferry to Fishers Island, New York, and I’ve even done Cross Sound’s Classic Lighthouse Cruise out of New London. I figured it was about time I took the ferry to Long Island.

Booking The Ferry To Get To Long Island

You can easily book the ferry online on Cross Sound Ferry’s website. You can book it as just a passenger or to bring a car with you.

We brought a car with us because Orient Point is a bit rural. Having a car with us was the easiest way for us to get around. It was more expensive, but I don’t mind paying more to have my own vehicle so I can explore at my own pace.

If you’re bringing a car, you’ll have to give the make and model of the vehicle you’re planning to bring. If your vehicle is over 20 feet, you will have to pay an additional fee.

Getting To Cross Sound Ferry

Cross Sound Ferry’s terminal is in New London, Connecticut. It’s next to the train station on Water Street. The easiest way to get here is to take I-95 and take the exit that takes you to the New London Waterfront.

Have your reservation documents ready when you get there. They will need to scan your reservation to give you your tickets for the actual ferry.

If you’re taking a vehicle with you, they will direct you to a lane to pull into. You’ll likely have the option to go in the standby lane to get on an earlier ship. We did this and were able to catch the 6:30am trip instead of the 7am trip we had booked.

If you’re going over as a passenger without a vehicle, there is limited parking at Cross Sound Ferry for $15 per calendar day. You can also park in the Water Street Garage, which is also paid parking. The Water Street Garage is directly across the street and a short and easy walk to the terminal.

Boarding The Ferry

If you’re taking a vehicle, the staff will direct you on to the boat and where to park. For those of you that have never taken a vehicle on a ferry, they pack the cars VERY tightly together, especially if it’s a fully booked trip.

There is a chance you’ll have to squeeze out of your car and then make your way through the other tightly packed vehicles to get to the stairway to the seating. It’s a good idea to put your mirrors in. If you’re just a passenger, you won’t have to deal with any of this.

The available seating will depend on which boat you end up on. Cross Sound Ferry has 11 boats total. For the trip out, we were on the JENNIFER C, which was originally built in 1965 as the M/V PAMLICO by New Bern Shipyard in New Bern, North Carolina for the North Carolina Department of Transportation Ferry Division.

Most of their ships have indoor and outdoor seating available. Inside you’ll find a galley with plenty of food and drink options, bathrooms, seats, and tables. Most of the ships also have outlets if you’d like to catch up on some work while you travel or if you need to charge your phone.

The Ferry Ride To Long Island

As you make your way to Orient Point, you’ll get to see some points of interest. As I was leaving, I actually got to see a cruise ship coming into the port of New London, which I thought was pretty cool. I knew they came to New London, but I’d never actually seen one there.

After, we cruised past Fort Trumbull State Park. Fort Trumbull has a legacy of service spanning two and a half centuries, from the American Revolution to World War II to the Cold War. It’s definitely worth a visit if you get the chance! There’s a great museum and you can actually go inside the fort as well.

Next, we sailed past New London Ledge Light and New London Harbor Light. Since it was very early in the morning, the lighting was great for New London Harbor Light, but not so much for New London Ledge Light. 

After we sailed past those, I went inside the cabin. I sat at one of the tables and did a little bit of work until we got a little bit closer to Long Island. 

I went back outside as we neared Orient Point Lighthouse. Close to Orient Point Lighthouse, you’ll also see Plum Island Lighthouse. 

As you get closer to the Orient Point Terminal, there will be an announcement letting you know you can go back to your vehicle if you took a car. If you were just a passenger, the announcement for you will be after the vehicle passengers get into their cars. Then, you’ll be able to get off the ferry.

First Stop: Fire Island Lighthouse

When we got off the ferry, we started to make our way to Fire Island Lighthouse. This lighthouse was not at all close and it was not a part of our original plan. But, since we were able to arrive in Long Island 30 minutes earlier than anticipated, we decided to go for it. 

Fire Island Lighthouse is 80 miles away from the Orient Point Ferry Terminal. The drive took us a little under two hours. We parked in the Robert Moses Field #5 parking lot to access the lighthouse. 

From the parking lot, we walked the boardwalk to the lighthouse. The boardwalk is a fairly easy .75 mile walk.

If you don’t want to walk, there’s also a pedicab that will take you right to the lighthouse from Robert Moses Field #5 parking lot.

At the lighthouse, you can visit the lighthouse, the Keeper’s Quarters, the Lens Building, the Boat House, and many exhibits for a unique journey through history.

Unfortunately, we didn’t have a ton of time at the lighthouse so we couldn’t thoroughly explore the grounds. But, we did climb the lighthouse. It’s 182 steps to get to the top with a handful of landings to take a breather as you go up.

This lighthouse is the tallest one in New York State. From the top, you’ll be rewarded with 360-degree views of the Atlantic Ocean, Fire Island National Seashore, Long Island’s bays, and even the Manhattan skyline.

We also took a peak inside the museum and the lens building while we were there. Then, we had to make our way back down the boardwalk to make our way back towards Orient Point. We had a lighthouse cruise at 2pm and we needed to get there 30 minutes before sailing time.

Second Stop: Lunch at Angel’s Country Store

We decided to grab lunch at Angel’s Country Store. I picked this spot because it was only 10 minutes from the ferry terminal. I got a chili dog that was pretty good. They had some indoor and outdoor seating available, but we ended up taking our food to go to eat at the ferry terminal.

Third Stop: Back To Orient Point Ferry Terminal For The Lighthouse Cruise

We ate lunch under the pavilion by the ferries. There was also a small beach by the terminal you could walk along. The views were great.

30 minutes before the cruise, we checked in at the small booth to get our tickets for the lighthouse cruise. Then, we lined up to wait to board.

The Long Island Lighthouse Cruise with Cross Sound Ferry

The boat was a high-speed passenger boat that they use for the Block Island Express as well. There was an air-conditioned cabin with a galley and bathrooms as well as outdoor seating. We sat on the top deck of the boat by the bow.

The tour was a two hour narrated cruise. We saw a total of eight lighthouses on the cruise. Below are the lighthouses we saw.

Little Gull Island Light

Little Gull Island is located in Southold, New York. It’s located on a small island that’s located midway between Plum Island and Fishers Island. The current lighthouse tower was built in 1869.

Race Rock Lighthouse

Race Rock Lighthouse is located off of the southwest edge of Fishers Island in New York. This lighthouse was completed in 1878. It’s said to be one of New England’s most haunted lighthouses. It was actually investigated by Ghost Hunters. If you’re into that kind of stuff, the episode is definitely worth a watch because they caught some pretty interesting evidence.

North Dumpling Lighthouse

North Dumpling Island Lighthouse is also located off of Fishers Island. This lighthouse is privately owned. The lighthouse was built in 1849, rebuilt in 1871, and deactivated in 1959.

Avery Point Lighthouse

While we didn’t get too close to this lighthouse, we did get to see it in the distance. This lighthouse is located at UConn’s Avery Point campus in Groton, Connecticut. You can actually visit this lighthouse up close as the campus is open to the public. Built in 1943, this is Connecticut’s newest lighthouse.

New London Harbor Light

The next Connecticut lighthouse you’ll see on the tour is New London Harbor Lighthouse. This lighthouse is both the oldest and tallest lighthouse in Connecticut and on Long Island Sound. The lighthouse was established in 1760, but the current tower you see today was built in 1801. This lighthouse is owned by the New London Maritime Society and you can actually climb it.

New London Ledge Light

The last Connecticut lighthouse you’ll see on this tour is New London Ledge Light. This lighthouse is also said to be haunted. The story is that this lighthouse is haunted by a ghost named Ernie who jumped from the lighthouse after his wife left him for a ferry captain. This lighthouse is also available to tour with the New London Maritime Society.

Orient Point Lighthouse

Orient Point Lighthouse is a sparkplug lighthouse that’s off of the coast of Orient Point, New York. You’ll often hear this lighthouse referred to as “the coffee pot.” This is because it was originally painted brown. The lighthouse was built in 1899. Today it is home to the Orient Lighthouse Artist Residency.

Plum Island Lighthouse

Plum Island Lighthouse is located on Plum Island not far from Orient Point Lighthouse. This lighthouse was built in 1869. There are a handful of lighthouses with this exact design, including Sheffield Island Lighthouse in Norwalk, Connecticut and Morgan Point Lighthouse in Noank, Connecticut.

Fourth Stop: Greenport, New York

After we got off the ferry, we decided to go into the village of Greenport. Greenport is a historic village on the North Fork of Long Island. Between 1795 and 1859 Greenport became a major whaling port with twenty-four whaling ships making a total of 103 voyages.

There’s also a lot of railroad history in town. The Greenport terminal of the Long Island Railroad was an important force in the commercial development of Long Island.

The farmers in North Fork utilized trains dispatched out of Greenport to take their harvest to markets in the west. Many of the historic railroad structures have been preserved by Greenport’s Long Island Railroad Museum, including one of only three steam-powered turntables in existence.

In town, we grabbed dinner at 1943 Pizza Bar. This spot serves up delicious brick-oven pizza. We got a pepperoni pizza. Can’t go wrong with pizza in New York.

After, we checked out the Ireland House. This is the home of Stirling Historical Society of Greenport. It serves as a museum, but it wasn’t open when we went. Even though it wasn’t open, I wanted to take a look at it since we were walking by. I’d definitely like to check this museum out when it’s open.

After, we grabbed some ice cream at Greenport Creamery. This spot serves up homemade ice cream, with over 45 flavors to choose from. They also offer dairy-free flavors.

After, we headed down to the waterfront by the antique carousel. The Carousel was built in 1920 and moved to its current location in 2001. It’s only a couple dollars to ride the carousel.

This waterfront park also has a camera obscura. A camera obscura is a darkened room into which light enters through a small opening, projecting a live picture onto a screen. This wasn’t open when we went, but I’d love to check it out into the future.

fifth Stop: Orient Beach State Park

We decided to head to Orient Beach State Park before heading to the ferry terminal since it was basically next to the terminal. We drove the road all the way down to the beach. There was a playground, a large beach area, and picnic areas.

The Ferry Ride Back To Connecticut

After, it was time to take the ferry back. We were supposed to take the 8:30pm ferry, but thankfully we were able to get 8pm ferry. I was happy to get this earlier ferry so we still had some lingering light from the sunset to be able to enjoy some views as we cruised back.

We ended up on their largest ship, the John H., which was built exclusively for Cross Sound Ferry. It is the largest ferry in their fleet and it’s able to carry 100 vehicles and 1000 passengers. This is probably my favorite ship in the fleet just due to its size. We spent our time on the spacious top deck as we made our way back.

Is This Day Trip Worth Taking?

Absolutely!! I’m already itching to take the ferry back out to the Long Island for another day trip. I barely scratched the surface of things to do during my trip. I saw a lot of historic sites I’d like to check out in addition to vineyards and museums on the North Fork. I definitely would stay on that section of the island if I were to make the trip from New London again.

In the future, I’d also like to take the ferry from Bridgeport, Connecticut to Long Island, New York. This would have been the ideal ferry to take for a trip to Fire Island, but I just had my heart set on visiting a lighthouse. The lighthouse that was closer to where we were (Horton Point Lighthouse) was not open that day.

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