I’m always looking for towns that offer the trifecta: arts, food, and outdoors. Woodstock, New York hits all three. Best known for the name of the 1969 music festival – which was actually held in Bethel – Woodstock still maintains its hippie roots. Peace signs, tie-dye, and music color the town. Woodstock’s main street is lively and a great place to spend an afternoon browsing and eating.

Woodstock has several live music venues that host bands every night of the week. While I was there, I checked out the infamous weekly open mic night at The Colony. I always love the vibe of a local open mic night because you get an eclectic mix of what the area has to offer without having to commit to an artist that you don’t know anything about. The Colony’s did not disappoint.

Looking at options for local hiking, I came across Overlook Mountain that not only boasts a lovely view of the Hudson River Valley and a 60 ft observation tower, but also the ruins of The Overlook Mountain House: a luxury hotel built in the early 1900s. It is definitely a hike, so come prepared with proper clothing and water, but it is well worth it. Ruins of old buildings are always fascinating to me because they always make me think about what life was like in the past.

Near the trailhead of Overlook Mountain are two religious sites that were worth the short drive in themself.

The first glimpse of the Karma Triyana Dharmachakra Monastery is the group of prayer flags coloring the trees. These set the airy and colorful vibe of the KTD Monastery.

While I was there on a weekday, so I didn’t get to participate in the formal tours they offer on weekends, I still was able to roam the grounds, check out the bookstore, and appreciate the vibrant sights and peaceful energy of the space.

Right around the corner is Woodstock’s oldest church, Church of Holy Transfiguration. Even when not in comparison to the KTD, this is a modest building. Consisting of one room, the Greek Orthodox Church of Holy Transfiguration was hand built in 1891 and has been lovingly taken care of by the members of the church since. I was pleasantly surprised that I could enter the space, so I took a few minutes to enjoy the dark and rich interior.

A few summers ago I acquired a river tube, so I’ve been looking for places to use it, and I found that in nearby Phoenicia, you can tube the Esopus river – I used Tinker Tubes to set me up with equipment and a ride. It was a pretty action packed ride for tubing, so I was glad they offered a helmet & life jacket.

This meant that I started looking into other places to explore in the Phoenicia area. I ended up finding so many interesting places to stop, starting with the Emerson Kaleidoscope. This is housed in the lobby of The Emerson Resort & Spa, so I didn’t really know what to expect going into it. It is actually the world’s largest kaleidoscope (verified by Guinness World Records in 1997). For a small fee, you can experience a 10 minute show inside the kaleidoscope that is a visual circus – it was pretty cool. The show doesn’t include any history, but the people who work at the attached gift shop were able to answer questions. The shop also has a vast collection of smaller kaleidoscopes (including the not verified “smallest kaleidoscope”) for sale and for viewing.

After checking out the small Phoenicia center, I hiked the short – but still a hike – Tanbark loop, which offers some nice views of the area.

On the way back to Woodstock, I came upon the Catskills Visitor Center. I always enjoy stopping by a visitor center to get ideas for other adventures and to talk to the staff if they are around. This one also boasts a small sculpture garden, with some of the art pieces made out of recycled material. It was a nice surprise. They also told me of the nearby Ashokan Reservoir, so I decided to add in one more stop before heading back to my place.

With a paved path across the reservoir, and parking on either side, The Ashokan Reservoir is a nice easy way to stretch your legs and experience a lovely vista. After a long day, I didn’t do the complete 5.4 mile out and back path, but I think it would be lovely to make this the main walk of your day. Because it is paved, you can roller skate, bike ride, or wheelchair the path.

On a hot day in the summer, there are also a few swimming holes to check out in the area. I stopped by the Big Deep swimming hole, which is located in the woods with no clear signage for parking. I have heard that many of these swimming holes have closed because of irresponsible visitors, so if you go check to see if they are still open & be kind to nature so that future visitors can enjoy the space too.

In the end, I came for the music, but I found peace in all forms. It was a lovely area that I want to explore more.