On This Full-Day Fall Foliage Cruise, I Got to Experience the Best of Autumn in New York

On one of the very first brisk Saturday mornings in September, I found myself walking up to Pier 83 in Midtown Manhattan. Moments later, I was met by my friend Lex, who was carrying two seasonal lattes to kick off our full day aboard Circle Line’s Bear Mountain Oktoberfest Cruise. I was first intrigued by the excursion—which brings you up the tree-lined Hudson River and drops you off in beautiful Bear Mountain State Park (about 45 miles north) for a few hours before returning to Midtown—after deciding 2026 was my year to prioritize the magic of fall in NYC. I've spent the past four years living in the Big Apple, but the months between August and December have always been bursting at the seams with classes and multiple jobs, leaving zero time for leisurely autumnal activities. Now that my schedule has relaxed a bit, this sailing felt like an ideal way to kick off the season, promising eight hours of leaf-peeping, hiking, live music, and Oktoberfest-inspired refreshments.The Circle Line boat docked at Bear Mountain State Park ElleAnna RevellViews from the middle of Hassain Lake ElleAnna RevellStepping aboard the Circle Line ship, my friend and I were greeted by a few lovely staff members who verified our tickets and sent us on our way to explore a bit before choosing our seats. We entered on the main floor of the boat, which had enclosed seating and the main concessions area, all decorated to fit the Oktoberfest theme. On the second level, we found a bar with additional indoor and open-air seating, while the third level was available only to those with premier tickets, which we learned grant you access to a private bar and restrooms, plus unlimited soft drinks and a German-style food platter. We snagged two open-air seats on the second level and settled in for the ride up to Bear Mountain State Park.Lex and I enjoying our spontaneous paddleboating adventure ElleAnna RevellThe morning sun was shining as the ship departed at 9 a.m. sharp and began trailing up the west side of Manhattan. I particularly enjoyed this part of the ride because I got to watch from afar as we passed one of my favorite sections of the Hudson River Greenway. We listened to our friendly tour guide, David, a former acting and public speaking professor, share every local and historical fact imaginable while taking in the scenery. Because it was September, the leaves had not yet made their vibrant transformation, so I can only imagine how breathtaking the already gorgeous views will be during peak season.Lex and I spent the first hour chatting and keeping warm under the hats she brought along. I made the mistake of only looking at the high of 72 degrees when checking the weather, and not accounting for the morning chill. If you do choose to sit outside, know that it can be quite windy and a bit chilly, especially in the mornings. I would recommend easy-to-remove layers (you will definitely warm up later!) and a cozy hat.A delicious soft pretzel ElleAnna RevellA glimpse of what the leaves will look like in peak season Circle Line CruisesBy 10 a.m., the chill in the air had subsided, and we were feeling ready to indulge in some Oktoberfest fare. Even though it was still early, we started at the bar—because why not! We certainly weren't the only ones—most people on board (of whom I'd guess 70% were visitors from out of town) had already started drinking, and the vibes were high. Lex went with a pumpkin beer, which solidified the already autumnal ambiance. As the resident gluten-intolerant, I opted for white wine. Downstairs, the food options ranged from hot dogs and nachos to a plethora of baked goods and German-style plates. Lex chose a hot dog and a massive soft pretzel, and I went with nachos and a protein box. The food wasn't my personal highlight; it was similar to what you might find at a sporting-event concession stand. However, Lex was a huge fan of her snacks. As we finished up eating, the band, Divining Rod Band, made its first appearance, performing a mix of folk and country songs—a fantastic complement to the views.After about three hours on the water, we arrived at the Bear Mountain State Park dock, where we got off and were led up a winding path that offered scenic views of Bear Mountain Bridge. On the way up, we veered off the walkway onto a section of the Appalachian Trail, and within five minutes, we nearly bumped into a baby deer and its mother. I grew up in a section of the Appalachian Mountains, so this was an especially nostalgic moment for me. Once we reached the top of the original path, we were greeted with a glistening view of Hessian Lake. Picnic tables lined the water, filled with groups enjoying the early fall afternoon and last rays of September sun.Our view from the second-level open-air setting ElleAnna RevellA perfect baby deer on the Appalachian Trail ElleAnna RevellAs my friend and I made our way around the lake, we spotted a paddleboat rental shack. It took very little convincing and only $10 a person for us to end up in the middle of the water. I have never paddleboated before, but I would highly recommend the experience—it reminded us both of childhood days out on the lake. Attempting to pedal across the water was quite amusing and also a fantastic leg workout.We then kept the workout going by taking on one of the park's many hiking trails, heading upwards on another section of the Appalachian Trail behind Hassain Lake. The path was lined with stone steps and gorgeous clearings overlooking the water. We made a much-needed pit stop, lying on a large rock and staring up at the crystal-clear sky, and then it was time to begin the voyage back to Manhattan.Everyone aboard was obviously a bit tired and very content to sit back and enjoy the serene views as we headed south towards the city. My friend and I grabbed some chips and sodas for a little pick-me-up before settling back into our seats. We chatted about how we hadn't felt inclined to reach for our phones throughout the day, and how nice it was to be outside rather than online. The Oktoberfest vibes continued throughout the ship with more live music, and the pumpkin beer never stopped flowing.The band playing for passengers ElleAnna RevellPicturesque picnic tables around Hassain Lake ElleAnna RevellOur boat arrived back in Manhattan just after 5 p.m., and we were quite happy to be back on solid ground following eight hours on the water. After a day full of fall-centric activities I wouldn’t normally seek out on my own, my excitement for the coming months in NYC had only grown. I also felt so grateful to have spent a full day with my friend, something that isn't always easy with busy, conflicting schedules.This one-of-a-kind cruise experience combined the best aspects of autumn, making it the perfect kickoff to my very intentional fall season. If you're tired of doing the same thing every weekend and want a unique way to experience the season before the leaves start to fall, grab a friend (or two or three!) and hop aboard. I promise you won't regret it.About Circle Line CruisesCircle Line was founded in 1945 by Frank Barry and Joe Moran, along with a few partners who merged several competing boat companies to form Circle Line. Since then, over 85 million passengers have been welcomed aboard its numerous cruise experiences, which range from holiday lights tours to summer sunset experiences. Circle Line currently occupies two docks in NYC. Pier 83 is the starting point for experiences like Best of New York, Landmarks, Liberty Midtown, and Harbor Lights, while Pier 16 hosts the Liberty Super Express and Statue at Sunset.How to book the Bear Mountain Oktoberfest CruiseThe Bear Mountain Oktoberfest Cruise can be booked directly through the Circle Line website. The experience runs every Saturday and Sunday from September 19 through November 8 for optimal leaf-peeping. If you are interested in a fall cruise but don’t want a full-day activity, Circle Line's Hudson River Fall Foliage Cruise is another great option. It’s a four-hour boat ride that takes you up to Hook Mountain State Park and back down to Manhattan, with the same onboard amenities and Oktoberfest theme as the Bear Mountain State Park sailing.