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Chasing Waterfalls and Wineries in Upstate New York

Road trips are one of my favorite ways to explore. Ever since moving to Chicago, I don’t take as many road trips anymore. So, when I got an offer to road trip through upstate NY for a few days to see waterfalls and try some new wineries, I jumped on it. As always, I try to maximize every trip and when possible combine a work trip with a bit of fun. This trip was exactly that: work for a few hours each day and then exploring the rest.


It was my first time seeing the full state of NY and it was beautiful. We flew into Albany and spent the first night there before getting up early the next day to begin our drive north to Watertown to check off a few work items. Once in Watertown, we stopped at a Cider Mill, called Burrville Cider Mill. It was a cute spot off a small rural road that made one of the best apple pies I have ever tasted. We also tried their cider, cheese curds, and fudge while watching a the waterfalls in their backyard. The combination of rich food and peaceful sounds of running water was a perfect way to end a work-filled Monday. After we checked into our hotel, we found a small Italian spot called Pete’s Trattoria for dinner. It had a family style feel with a simple kind of charm you would expect from a local Italian spot. We ordered bruschetta, burrata, Italian hot peppers, and gnocchi. The pasta is homemade and delicious so if you are in the area, give this spot a try.


The next morning, we drove south toward the Finger Lakes, stopping at a few wineries along the way. The first one we stopped at was Fox Run, with a back patio that overlooked the lake. We did a tasting ($7) and ended up enjoying their canned Riesling the best because it was was refreshing and light. The second winery we stopped at was Pompous Ass. In full disclosure, we stopped here because of the name, but the wines were so good we actually bought a bottle of their Riesling to drink later with dinner. (The tasting was $12.) We are not big Riesling people, but somehow enjoyed that wine the most at both spots. The Finger Lakes have plenty of other wineries to check out and we wished we had more time to do a true wine trail tour of the area. The best advice I have if you are looking to hit up wineries while you’re in the region, is reading reviews about the wineries that are within 30min of where you stay. If you’ve never done a winery tour, make sure you look at the reviews of the tours as well and not just the wines. We made our choices based off good views and an entertaining name. But you can’t go wrong!

The last stop for our day before we found a hotel was Watkins Glen State Park. The park is free, but parking is not (~$10). The main trail, Gorge Trail, takes you straight through the cavern and follows the path of the river allowing you to see all the waterfalls. The entire loop is about 2 miles and takes 1hr if you stop to take pictures and look at the views. I would recommend wearing some type of shoe with a grip (sneakers) because the rocks get slick, but the path is very clear and laid out in stone in some places. After leaving Watkins Glen, we started looking for a place to stay. We read a few basic reviews of the hotels in the area and chose a potentially questionable cabin spot about 10 minutes outside the town of Watkins Glen called Lakeside Resort. The name sounded nice and the premise of renting your own cabin that overlooked the lake was right up our ally. However, there was very little information, reviews, or pictures of the spot so we took a gamble and drove to check it out. Not only did this place not disappoint, but it FAR exceeded our expectations! They had just gone through renovations and the main house had a rustic bar with a large living room area and windows that overlooked the back of the property. There was a fire pit with adirondack chairs outback with a view of all the personal cabins lined up along the path leading down to the lake. Because we were walk-ins, we got 20% off a cabin with a king bed and full kitchen (normal price is $180). The cabin was brand new with a gorgeous bathroom and a personal back porch that overlooked the water. We loved the spot so much that we ended up ordering pizza to go from Jerlando’s just so that we could eat in front of the fire pit with the lake in the background, while drinking our bottle of Riesling from Pompous Ass. As it turned out, the part of our trip that we didn’t plan was the highlight! The staff were all very friendly and included a complimentary breakfast with our stay. All in all, Lakeside Resort was incredible and I would recommend it to anyone passing through the area or looking for a quiet getaway in upstate NY.


We spent our last day driving to Niagara Falls to take the Maid of the Mist boat tour from the NY side. The Canadian side is filled with casinos and extra forms of entertainment that detract from the natural beauty of the falls (in my opinion) so we stayed on the New York side. The Maid of the Mist tour takes you straight into the heart of the falls so you are surrounded by waterfalls on 3 sides. You get drenched but it is worth it to be enveloped by the falls. It was my first time seeing Niagara falls, so to say that I couldn’t stop staring is an understatement. We had to drag ourselves away from the viewing decks to get back in the car and make it to Jamestown in time to check into our hotel, the Chautauqua Harbor Hotel. The hotel overlooked the lake and was in a more secluded part of town. We were pretty tired from our day so after a quick workout we grabbed dinner in the hotel restaurant and then just enjoyed the view of the lake with drinks in hand.


While I only saw a small piece of upstate NY, I was easily convinced of its beauty and would love to explore more one day. For more details on the Finger Lakes region, I recommend checking out this site: https://www.fingerlakes.org/


For any questions about this trip or others, connect with me on IG. We all find different favorites in each place we visit and I would love to hear from you about what you’ve experienced.

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