If you read our post on places to hike and swim in the Hudson Valley, you already know that I recently went to Woodstock to hike in the Overlook Mountain Forest. We spent a little bit of time in the town to fuel ourselves up for the hike. On our last local adventure, we did a little shopping and eating in New Paltz, a paired activity I can never turn down around the Valley. Here’s a rundown of what I did while in Woodstock – though the town is certainly busy enough to warrant another trip!

Local Adventures: A Day in Woodstock

Food: Bread Alone

We started our hiking day with a food stop at Bread Alone. I split the Mediterranean sandwich and the Spelt Berry Salad with my mom and my dad had the Chicken Club. We love Bread Alone’s bread, I have a piece of their sourdough toast almost everyday. Since we’re such big fans, we made sure to get a loaf for later – we went with the Peasant loaf. I’ve also been attempting to cut out coffee from my diet, so I opted for an iced chai latte.

Shopping: Woodstock Flea Market

To digest our lunch a little bit before our hike, we walked around the Woodstock Flea Market. They have lots of different vendors where you can find art, vintage jewelry, records, drums, any color of cowboy boots, and naturally dyed clothing. I didn’t pick anything up (which required a lot of self control!), but it was lovely to walk around and see everyone’s tables.

Hiking: Overlook Fire Tower

Once we felt mentally and physically ready for our hike we drove over to the Overlook Mountain Trailhead. This hike was a pretty steep incline the whole way up. I took a couple of breaks to sip some water, but the way up took about an hour and was 2.5 miles one way.

The Overlook Mountain House Ruins are beautiful at this time of the year. I loved looking through different windows and seeing the frames they created of the trees, vines, and other parts of the building. The pockets of light in the shadows of the walls felt so magical a well. I took my time exploring the site, going up and down steps and walking around the ruin.

Once I made it to the ruins, only a 5-10 minute hike remained to reach the fire tower. The ruins really gave me that final push!

This day was incredibly windy and we were definitely feeling the wind up there. It was pretty wild walking up the fire tower with non stop gushing wind, but thankfully the fire tower was very sturdy and didn’t make any creaking noises to make me nervous. Plus, I knew that the panoramic view would be worth it.

Thankfully the windows at the top of the fire tower were all closed except for one. It was fitting that we earned some calm after all of those steps – especially paired with a breathtaking view. After a nice reset and lots of admiration of the view, we headed back down to soil.

A 2 minute walk in the opposite direction had a cliff overlook that was stunning. We could see the Hudson River and the Ashokan Reservoir. We sat there for around 15 minutes before heading back down.

It was such a lovely day and believe it or not, it was chilly on the way back after all of that cooling wind. I highly recommend this hike! It was not crowded and was so much fun. I’m looking forward to going back!