You have to get out of Bennington sometimes, and the beauty of “The Benn” is that there’s always something to do right up the road. Every Columbus Day weekend, Stratton Mountain hosts the Harvest Fest and Chili Cookoff and it’s totally worth the trip up, no skiing necessary!

We had never been to Stratton before, we’d driven up to Bromley (Bromley is a smaller, south-facing mountain known as Vermont’s “Sun Mountain” and Stratton is larger and more corporate and faces north. But I’m okay with corporate things (ya’ll know I shop at Walmart lol) so I was psyched to get to Stratton and I wasn’t disappointed.

We walked around the village to start, I loved it! It’s so funny because I had kept going on and on about how unpretentious Vermont is, how people frown on fancy cars and $500 shoes and labels mean nothing to them, but lo and behold, when I hit Stratton Village I had to rethink all that. I could easily have spent $5000 that day, just on all of the adorable winter and ski wear (I don’t ski – yet) but I can rock some skintight ski pants and a Canada Goose puffer, trust me, and don’t even get me started on the boots, the ski shops have tons of European brands plus your basics, Marmot, Burton, Helly Hansen, you feel me. I need to NOT go to Stratton Village if I have any hope of keeping my credit intact, but if you’re looking for really high-quality (and, sadly, high-priced) outdoor wear by all means be my guest! It’s kind of a cute little village too, I mean, it’s not huge but worth a half day trip.

The Harvest Fest turned out to be really all about drinking, which is fine, we don’t drink but same as with the $1500 parkas, be my guest! But I thought there would be more food there too, and there really wasn’t. They have bands though, and a chili cookoff, and it’s a very instagrammable, well-heeled crowd up there. So instead of doing the festival thing, we opted to hike up the mountain, and I’m sharing a few of my fave shots here.

We decided not to eat in the village but drove back down towards Manchester to the Raven’s Den. We had some nachos and hung out for awhile, we just enjoyed relaxing and watching the people. This was the absolute height of the foliage, so like, everyone was Boston and NYC was up in their Escalades, I’ve gotten really used to seeing people in 10 year-old Subarus and even older hiking boots, so I got a real kick out of seeing all of the stylish city folk in their Hunters and Barbour. And the one little tiny thing I did feel like I could afford (lol I just bought a second home so… was this little headwrap by Skida, I don’t ski but who can’t use a headwrap up here?

But the Harvest Fest is so worth the trip, just keep in mind you’ll want to eat in a restaurant in the Village or on the way up, and if you walk up even part of the mountain trust me, you’ll be needing food! Enjoy!