The Gateway to New England: Taking the Cross Sound Ferry from New York to Connecticut

What to expect – with pictures – if you plan to travel this way!

I recently traveled from Montauk, NY (on the East End of Long Island) to Boston, MA for a wedding. While Long Island is such a beautiful and fun place, traveling onto and off of Long Island can be difficult and painful. Fortunately, if you’re heading north to New England, you can avoid a lot of driving and traffic by taking the Cross Sound Ferry (which runs between Orient Point, NY and New London, CT).

If you’re making a similar journey, here’s what to expect and what you’ll experience as you take the Cross Sound Ferry.

Blue sign with gold-colored letters with blue sky and green trees in background
Welcome sign upon reaching the Cross Sound Ferry entrance in Orient Point, NY.

Travel Options: Driving vs. Ferry Boat

Fun fact: at 118 miles end-to-end, Long Island is both the longest and the largest island in the contiguous United States! But if you’re on the East End of Long Island and need to head north, that’s 118 extra miles you’ll need to drive. Moreover, you would need to drive west into Queens, cross a bridge north to the Bronx, and then drive east to reach New England destinations. Not only is this circuitous, but it involves driving through heavy urban traffic in New York City and on I-95 in Connecticut. Definitely not appealing!

You can see the different travel options in the below picture from Google Maps. For my trip from Montauk to Boston, taking the Cross Sound Ferry saves 114 miles and 30 minutes of driving (and that’s during a time when there’s little traffic – it could save hours when there’s heavy traffic on the roads!).

Google Maps travel routes with mileage and estimated travel time
Travel options from Montauk, NY to Boston, MA. Map data © 2021 Google.

Taking the ferry is also great if you’re traveling with young children – not only will it be quite memorable for the little ones, but you can also get out of your car to feed them, take them to the bathroom, and enjoy the view as you cross the water!

For a typical sedan or SUV plus driver, the Cross Sound Ferry costs $63. If you want priority service – meaning you’re one of the first cars to get on and off the ferry boat – it will cost $76 (at only $13 more, I highly recommend priority service!). Additional passengers (age 12+) cost about $20 each. Children (age 2-12) cost $7 each, and infants (age 0-2) are free.

Traveling from the Hamptons to Orient Point, NY

While I was traveling from Montauk, for most locations in the Hamptons you will first need to go through Shelter Island to get from the South Fork of Long Island to the North Fork. Shelter Island is only accessible via ferry: from North Haven using the south ferry and from Greenport using the north ferry.

Google Maps estimated it would take 2 hours to get from Montauk to Orient Point. With light traffic and quick Shelter Island ferry connections, it only took me 1:40.

View looking outward from a ferry boat onto blue water
View from the north ferry boat heading from Shelter Island to Greenport.

Travel time from Montauk to the south ferry of Shelter Island was 40 minutes. The south ferry ride is very short – only about 5 minutes – and costs $16 for a car and all passengers. Once on Shelter Island, is takes approximately 10-15 minutes to drive to the north ferry. The north ferry ride is a little longer – about 10 minutes – and costs $17 for a car and all passengers. Once you’re off of the north ferry and in Greenport, it only takes about 20 minutes to drive to Orient Point where you’ll board the Cross Sound Ferry.

White ferry boat with cars on blue water
Ferry boat heading toward Shelter Island.

If you have extra time and want to explore Shelter Island, I’ve written about the fantastic hiking trails at Mashomack Preserve previously. Vine Street Cafe is an excellent dining option, and you can taste the region’s local wines at White Oak Wine Garden. Note that all three of these destinations are located directly on the route you need to drive from the south ferry to the north ferry, so they’re very easy to get to!

Traveling Aboard the Cross Sound Ferry

Boarding the Cross Sound Ferry boat starts about 30 minutes before its departure time. You will be assigned to a designated lane to wait in until boarding occurs (depending on your ticket type and whether or not you purchased priority service):

Cars lined up in front of ferry boats
Vehicle waiting lanes before boarding the Cross Sound Ferry.

The Cross Sound Ferry boats are much larger than the ones you just took on Shelter Island! Here you can see the Susan Anne ferry boat approach in Orient Point, NY:

White Ferry Boat in blue-green water
The Susan Anne ferry boat operated by the Cross Sound Ferry.

And the Mary Ellen ferry boat docked in the New London, CT harbor:

White Ferry Boat in water docked at a harbor
The Mary Ellen ferry boat operated by the Cross Sound Ferry.

Loading the vehicles onto the boat won’t take too long, and the ferry boats leave right on time. Here’s a view of the cars lined up on the Cross Sound Ferry boat:

Cars on a ferry boat
Vehicles and passengers aboard the Cross Sound Ferry.

Once aboard, you can exit your car and head to the upper deck of the ferry boat. This is a view from the upper deck looking over the vehicles:

Vehicles on a ferry boat with blue water and blue sky in the background
Vehicles aboard the Cross Sound Ferry.

There is ample seating on the upper deck. If it’s a nice day out, there is bench seating available so you can enjoy the view:

Blue seating on a ferry boat
Bench seating is available on the upper deck of the Cross Sound Ferry so you can enjoy the view.

There are also two main sections of indoor seating, which also have several tables in case you need to do work (or feed your children!). There’s a larger main cabin on the upper deck:

Blue seats on a ferry boat with passengers
Indoor seating on the upper deck of the Cross Sound Ferry.

And a smaller section of indoor seating located a floor below, by the restrooms:

Blue seats on a ferry boat with passengers
Indoor seating on the middle deck of the Cross Sound Ferry.

As you approach New London, CT, you can see the New London Harbor Light:

White and black lighthouse in blue water
The New London Harbor Light, a lighthouse on the west side of the New London, CT harbor entrance.

And you can also see Fort Trumbull State Park:

Fort with American flag and green grass with blue water in foreground
Fort Trumbull State Park, located on the west side of the New London, CT harbor entrance.

The Cross Sound Ferry advertises that the ferry ride takes one hour and 20 minutes, and I found that was quite accurate. There’s no real announcement that you are close and that you need to get back in car (a staff member walks around to tell passengers) – so it’s a good idea to be mindful of time.

After disembarking in New London, CT, it takes 2 hours to drive to Boston.

So if you’re traveling from the East End of Long Island to New England, definitely consider taking the Cross Sound Ferry. It’s a better, easier way to make the trip!


Have you traveled via the Cross Sound Ferry? How was your travel experience? Let me know in the comments below!


Explore more at ProjectsByPeter.com/Projects


Post content, images, and featured image © 2021 ProjectsByPeter.com – All rights reserved.

Leave a Reply