A Long Weekend in Watkins Glen

Take vacations, go to as many places as you can. You can always make money, you can’t always make memories.


Ever since I moved to Pennsylvania, I had heard people talking about Watkins Glen, a small, but hearty town in the middle of the New York wine region. By the time we decided to go on vacation there we were bombarded with suggestions and knew there was no way we could visit them all in one trip, but were excited to see as much as we could.

While the trip started out mildly disastrous with our car attempting to break down and the downpour of the century happening right as we crossed the line between PA and NY, we ended up having an amazing time. So much so that a week after getting home we planned a trip back for Thanksgiving.

I hope you enjoy my photos, tips, and stories from my trip and can use them to plan your own! Looking for dog friendly trips? You’ve definitely come to the right blog post. Looking for a boozy trip? You’ve also come to the right post. Hiking? Got you covered.

Day 0.5 — Disaster-cation & Rain-cation

Our first half day was nothing but car trouble, a 4 hour drive, a soggy dog, a delayed by 2 hours dinner/hanger, and the most rain we’ve ever seen come down at once.

Day 1 — Hiking & A Smidge of Wine

There are very few vacations where we spend time in our hotel other than what is absolutely necessary to sleep and shower. This time, was pleasantly different. We rented an Airbnb in Montour Falls, a hop, skip, and a jump away from Watkins Glen. Turns out it was the cutest farmhouse, complete with eclectic decor, homey touches, and the nicest host you’ll ever meet. We had room to wear out our border collie, a place to hang out outside and grill, cozy areas to curl up and read, and even fresh baked cookies. Heaven!

Once we tore ourselves away from the house, we set out to explore and find a great brewery (my boyfriend’s only requirement for the trip). Our first stop landed us at Grist Iron Brewery. We sampled several beers and I found the only wine on the planet I have ever actually liked. Way to go Grist Iron!

Afterwards, we decided to explore Deckertown Falls. It was a 5 minute drive from Grist Iron and where we were staying and we heard it was a beautiful hike. The hike was barely half a mile (if that), but there were plenty of places to let Atlas swim and get great pictures.

After all of this, we were super hungry and decided to head to the harbor for a late lunch. The view was GORGEOUS. We sat with a beautiful view of the mountains, Seneca Lake, and tons of sail boats. Then it rained briefly… luckily it passed quickly and we were able to explore more of the harbor and go out on the jetty.

You’ll be shocked to hear that our raincation continued right as we got back to the farmhouse…just as dramatically as the first day.

Day 2 — More Hiking & More Than a Smidge of Wine

Watkins Glen surprised me on just how many places were dog friendly, and one surprised me by not being dog friendly. My only wish for the trip was to visit the Gorge Trail in Watkins Glen State Park. Google it. I’ll wait. SEE? It’s gorgeous. Unbeknownst to us as we drive up with our dog hanging his head out the window looking as happy as can be that the only trail in the park that is not dog friendly is…you guessed it… the Gorge Trail.

We’re adaptable.We hiked the upper trails and I, literally, ran down the Gorge Trail to see the waterfalls and then met up with my boyfriend and dog to walk the lower trails back to the car. The trail was very crowded but the upper and lower ones were quite deserted and lots of fun. It was much easier hiking than we were expecting, but we had a great time together and that was really the point.

One set of waterfalls was not enough. We ended up seeing a total of 4 different waterfalls that day driving around. I highly recommend seeing as many as possible. They are all very different and picturesque.

Later that day we wanted to try more of the breweries in town and grab a bite to eat. We ended up driving past (twice) Two Goats Brewing until we found the parking lot. Oops. Now, we always take our dog with us to these types of places because he loves it but it is more rare for all of us to be allowed inside. This place was incredible. Atlas was allowed inside and everywhere humans could go which made the experience even better. As I got the only thing on the menu, the best roast beef sandwich I’ve had in a long time, we sat and talked with a view of vineyards and the lake. YES PLEASE.

At this point, we weren’t ready to go back to the house. It hadn’t rained all day and we wanted to press our luck. We drove to Hazlitt Vineyards & Winery for some more drinks, a tasting, and to hang out. After introducing Atlas to 3 different bachelorette parties we decided to escape outside for some fresh air and less crowds. They have a fantastic patio overlooking a pond and the atmosphere was very relaxed yet fun. 10 minutes later…the downpour came back….with a vengeance.

My favorite part of the day was spent taking myself on a photography walk. Everyone else was tired and I wanted to enjoy the end of the day after the rain had passed. I took a walk down the road where we were staying and got some of the coolest shots I’ve ever taken. Thanks for the inspiration New York!

Day 3: Farmhouse & Goodbyes

Our last day wasn’t eventful by any means, but we really enjoyed it. We had come to know the host of the farmhouse and just spent the morning playing with Atlas, petting the various farm animals, and just enjoying a relaxing, rain-free morning.

Joke’s on us… our 4 hour drive home was gorgeous without a drop of rain.

My recommendations:

  • Grist Iron Brewery
  • Two Goats Brewing
  • Hazlitt Vineyards & Winery
  • Watkins Glen State Park
  • Deckertown Falls
  • Shequaga Falls
  • Wildwood Farms, Montour Falls AirBnb

3 thoughts on “A Long Weekend in Watkins Glen

  1. Great post. I grew up in Buffalo and visiting Watkins Glen was something literally everyone did at least once, but I haven’t heard the name in decades. I enjoyed this little trip down memory lane. Glad you had fun!


    1. Thanks so much! I’m so glad you enjoyed it! I’m from Virginia and had actually never heard of it until I moved to Pennsylvania 2 years ago. We loved it so much we’re going back in November.


Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s