Nothing makes me happier than seeing the mountains in the fall. Being surrounded by a sea of orange, yellow and red I feel transported to another world. I was so entranced last year by Max and I’s trip to the Catskills last October that I knew we needed to do it again and luckily, Max felt the same way. While we had an incredible trip in 2020, we did it a little differently this year, opting for an Airbnb in Windham with two of our couple friends instead of going solo to Woodstock. Here’s what we did this year and what we’d recommend.
Where We Stayed
While my brother has had some bad Airbnb experiences we got incredibly lucky with this cozy cabin. I absolutely loved the A-Frame living room with giant windows and the dogs loved the backyard. It was the perfect place to stay as a group because there was plenty of room to all hang out indoors and outside. Our first morning we cooked up a big breakfast and ate outside on the porch and I couldn’t have dreamed of a better start to the weekend. That night we grilled and cooked again at home but ate inside and all fit comfortably around the dining room table. We also played Catan, watched movies and sports, and had breakfast inside the next morning. If you’re going to be spending a considerable amount of time inside or cooking at home, this is a great place to be.
What We Did
Last year we stayed in the heart of the mountains, in Woodstock, and loved the accessibility to restaurants, hikes, and outdoor activities. Windham is a ski town further north and a little more isolated than Woodstock was. There weren’t as many restaurants as we saw in Woodstock so we opted for mostly home-cooked meals. However, the grocery store was at least 20 minutes away through the mountains so I’m not sure we’d want to go back up to Windham for a fall trip.
If you do choose to stay in Windham in the fall there are a lot of great outdoor drinking options. On Saturday we drove over to The Vineyard at Windham for a wine sampling and charcuterie lunch. It was a great place to hang out for a few hours and very easy to get to. We continued the day’s theme at West Kill Brewing, which was not as easy to get to but just as great in terms of atmosphere. They have live music in the fall and while we unfortunately missed most of the set but couldn’t have asked for a better location to spend the afternoon. It was perfectly nestled in a valley with incredible views of the mountains around us, which were just starting to change color.
On Sunday we went for a really lovely nature walk at The Windham Path. It’s a one-and-a-half-mile loop that’s kid and dog-friendly and only takes about an hour. I’d recommend everything we did for a great weekend in Windham.
What I Packed
We had absolutely perfect weather. I was comfortable, maybe even a little warm, in sweaters and jeans. I packed my favorite Abercrombie jeans – the high-rise ankle straight in black and blue, this perfect-length turtleneck sweater from Aritzia that I have in both beige and black, nicer heeled booties and comfortable block-heeled boots, my favorite Patagonia fleece, and these Alo leggings.
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