A Fall Weekend Guide to the Catskills & Hudson Valley
As some context, my boyfriend and I decided to take a long weekend in the Hudson Valley and Catskills in mid-October 2020. We are aware of the ongoing coronavirus crisis and advise any trips planned to err on the side of caution. Luckily, this drive was only about 2 two hours north of my apartment, and any busy attractions we did plan for were strictly by appointment/reservation only. We also avoided eating at restaurants themselves and opted for takeout, and attempted to do our trails early in the morning to beat any fall foliage crowds. As always, have fun and stay safe.
DAY 1 :
My boyfriend and I started off our morning heading north, where our first stop of the day was to go to the Perkins Memorial Tower at the peak of Bear Mountain. To our surprise, it was unfortunately closed. We walked around Hessian Lake at the base of the mountain, thinking we had just arrived early and the park road wasn’t open yet, but unfortunately the road leading to the peak never opened. Apparently it was due to coronavirus cases on the rise in that county, so they closed off certain areas. The lake was still pleasant and was an easy 1.4 mile loop.
For brunch, we headed to the college town of New Paltz, home to SUNY at New Paltz. New Paltz had a busy Main Street that had a variety of restaurants to choose from. We ended up ordered takeout from Main Street Bistro. I ordered the chicken & waffle and Gabe got the breakfast special. We drove 15-20 minute to Minnewaska State Park Preserve where we sat down and ate lunch. The park was very full and park rangers were very strict about the number of people coming into designated parking areas, so we weren’t able to park by Lake Minnewaska itself. We eventually made way to Awosting Falls. The trail is a paved, but steep winding path that leads to a waterfall and is adjacent to Peters Kill. There were many tourists and families in this area, so we didn’t dwell too much by the top of the Falls. The crowd thins out very quickly once you walk further down the trail, past the waterfall. We did see one nice couple that were painting the beautiful landscape and a group of people picnicking on a dried portion of the riverbed. When you leave the Minnewaska State Park Preserve and turn left onto US-44, there will be a few scenic overlooks where you can pull over and enjoy a great view of the Catskill region.
We started off our morning at Hessian Lake. Unfortunately the peak of Bear Mountain wasn’t open when we went.
When you walk the trail from the parking area(s), you’ll actually arrive at the top of the waterfall first.
Follow the trail down, you’ll meet the popular waterfall spot. Beware it can get steep, so be wary when with little children or the elderly.
Continue walking along the water to see beautiful fall foliage. There are some areas where you can actually go in the Peters Kill without getting your feet wet.
We then headed to our stay for the night in Ellenville, where we had booked a Tentrr — a no fuss, no gear needed camping experience. Tentrr is a unique camping experience where most sites are privately owned, like Airbnb. Our site came with a canvas tent already set up atop a wooden deck, a fire pit, Adirondack chairs, and more. We were able to gather around the campfire on a chilly autumn night, while also taking in the beautiful starry sky. You really take the starry sky for granted when you’re used to so much light pollution! You can read all about our Tentrr experience HERE.
Our first Tentrr experience! Of course we had to have a little photoshoot.
It unfortunately rained in the morning, so we couldn’t enjoy the sunrise from our tent, but this sunset was beautiful.
There were several Adirondack chairs for us to enjoy, whether it was to gather around the campfire or gaze at the stars.
DAY 2 :
After checking out, we started our morning at Rail Explorers USA in Phoenicia. We did the River Run in The Catskills, where you ride the historic Ulster & Delaware Railroad rails that run alongside the Esopus Creek. It’s an 8 mile round trip on a tandem rail bike (they also have quads for families) with electric pedal assist, so you can do the work, but don’t have to strain yourself too much. It’s a hand-free experience, so you can take pics all you want. They encourage you to bring a snack and drink to enjoy at the turnaround point. The total time was about 2.5 hours. We booked online and went for the 11am ride, but there are other tours that may pique your interest like the golden hour (sunset) tour, Beer & pretzel, and other seasonal tours. They also have divisions in Rhode Island and Las Vegas, if you are interested.
We originally wanted to grab lunch from the Phoenician Diner down the street, but we decided to just go directly to Kingston. We ordered the burger lunch special from The Anchor. The burger special was delicious and really hit the spot after our rail workout. We unfortunately were too early to check-in into our Airbnb, (Here is where we stayed!) so we tried to go somewhere scenic, despite it being rainy and gloomy outside. We ended up at at Kingston Point Beach, where you can park and face the Hudson River. We weren’t the only ones that parked at the beach to wait out the rain.
After checking in, showering, and resting a bit, we were on our way to the Great Jack O’Lantern Blaze in Croton-on-Hudson, which was a 1.5 hr drive back south. To our dismay, when we pulled up to the event entrance, the event was CANCELLED. A few employees stood out in the rain and told us of the unfortunate news due to safety issues regarding the rain earlier in the day. We’re not sure if that meant tree branches were everywhere or if there was some sort of mechanical and/or electrical issues, but we were disappointed that we drove so far just to be turned away. We were refunded, but I wish they could have sent us an email earlier in the day. The Great Jack O’Lantern Blaze occurs every year and if you do happen to go, I’m sure you’ll have a great time. I was really looking forward to seeing the fun pumpkin displays and the Instagram-worthy pumpkin tunnel.
Riding the rails in October was perfect timing.
You get to ride the rails through the trees, by local neighborhoods, and along the Esopus Creek.
Unfortunately, the Great Jack O’Lantern Blaze was cancelled the night we had a reservation. This is what we could have seen.
DAY 3 :
We started off our Saturday morning with a paved and flat trail at the Ashokan Reservoir Promenade. It is definitely not a hike, rather a nice walk adjacent to the Ashokan Reservoir — one of the reservoirs that is a source of NYC’s water supply! It has beautiful panoramic views of several peaks in the Catskills and informational kiosks along the path, where you can read more about the history of the reservoir and surrounding peaks. By the time we left around 10:30am, the path was occupied by families, couples, bikers, and even roller skaters!
Afterward, we made ourselves brunch with some of the leftover ingredients we had from the Tentrr before heading out to explore the town. We stayed in Kingston, which is along the Hudson River. Kingston has 3 distinct areas: the Uptown Stockade Area, the Midtown area, and the Downtown Waterfront area. We explored Uptown Kingston to explore the local shops. If we had made it earlier to Uptown, we could have strolled through the Kingston Farmers Market, which runs from 9am to 2pm. If you’re not spooked by cemeteries, there are a few picnic tables you can sit at in the Old Dutch Church cemetery. In October, you can take an Old Dutch Cemetery tour, where you can learn about the infamous Kingstonians buried in the cemetery. We also went on a free impromptu tour of the Volunteer Fireman’s Hall & Museum, where we learned some of the local history of the fire department in Kingston, as well as got to see old equipment and carriages (before cars were invented!). Many of the smaller shops and cafes were closed, so we stopped by Hannaford Supermarket to grab a few snacks and went back to Kingston Point Beach to people and seagull watch. It was a much better experience this time around since it wasn’t raining. Afterward, we walked along the Kingston waterfront, which has a view of of the Rondout Creek. There are plenty of benches you can sit on and people watch from. If you have the time, check out the Hudson River Maritime Museum and Trolley Museum of New York nearby.
Don’t be spooked by the Old Dutch Cemetery. It was actually pretty peaceful to sit at the picnic tables that were in the cemetery.
We eventually walked around Uptown Kingston, where they had some cute boutiques, cafes, and more. They also had an LGBTQ Community Center.
Kingston Point Beach is a small beach but it has a view of the Kingston-Rhinecliff Bridge in the background.
Walking along the Kingston waterfront was a lively endeavor. Many people were out enjoying the sunset.
DAY 4 :
On our way back south, we stopped by Untermyer Gardens Conservancy in Yonkers for our 11:30am reservation. Untermyer Gardens Conservancy is a non-profit organization that partners with Yonkers in the restoration of the Samuel Untermyer Gardens — a beautifully landscaped garden that overlooks the Hudson River that was originally designed in 1916. The Gardens has a beautiful set of descending stairs and many photo opportunities. You don’t think you’re in New York, nor do you think you’re looking across at New Jersey! The Gardens are currently operating daily from 9am-4pm. When we went, the Gardens were by reservation only and only operated Friday thru Sunday, but they have changed their operation times. I found that some of the other tourists here were quite rude, especially when you were trying to take photos. We had no control over this obviously. Also, we didn’t realize that much of the garden loop was on grassy, uphill pathways, just so you know. But you do have some great photo opportunities here if you can wait out the groups.
If you time it right, you can get this area all to yourself.
It’s a long way down, so be sure you’re done looking at things at the top of the descending staircase.
There are also other areas where you can pose among colonnades, trellises, and water features.
We had a great 3 and a half day weekend and loved seeing the Catskills and Hudson Valley region. We had other things planned, but coronavirus and the rain had other plans for us. Had we gone maybe a week later, we could have seen even more sights at their peak foliage. If we had more time, we would have checked out the following sites:
Croton Gorge Park
Mohonk Mountain House, Mohonk Lake, and Sky Top Tower
Woodstock
Ferncliff Forest and its Fire Tower
Tivoli Bays
Saugerties Lighthouse
Kaaterskill Falls
Dia: Beacon and Beacon, NY
Storm King Art Center
GENERAL TIPS:
Always check sites for updated COVID-19 closures and policies. Policies changed very quickly from when we planned the trip, when we actually went, to when this post has been published.
Download offline maps ahead of time, as well as any songs or podcasts you would like to listen to. We encountered several dead service areas.
Be flexible. I am a major trip planner, so when sites were closed or rained out, I was very disappointed, but we made it work.
Bring quarters for parking in Uptown Kingston. There’s regular paid parking on N. Front St., by Kingston Consignments, but there’s plenty of metered parking everywhere else.
Pack layers for this time of year because you never know.
Check out AllTrails to browse and plan ahead the trails you want to go on. You can filter by difficulty, length, etc.