River Walks to Grilled Cheese: A Farewell to Great Barrington

I’m on my way back to New York City for the first time since January. It’s been a slow stretch — so slow, in fact, I’ve found myself wishing my dog Roxy could speak English just to spice things up. Still, there are a few hidden gems around my hometown, Great Barrington, that remind me there’s charm in the quiet.

First off, the River Walk. It winds alongside views of the Housatonic River and eventually leads into a maze of beautiful trees before opening up to a long, grassy field where the only soundtrack is the wind. It’s peaceful in a way only small towns can pull off.

After my walk, my mom and I made a pit stop at the local co-op market. It used to be wildly seedy (think: herbal teas that looked like spells), but it recently got a glow-up. Now it strikes the perfect balance of organic and modern. We grabbed iced teas and house-made smoothies that were surprisingly delicious.

The next day, I headed to Rubi’s Café, where I ordered a top-notch grilled cheese and a hot black coffee. It’s a great place to sit outside and catch up with the locals—most of whom are either artists, philosophers, or both. The café is in a gorgeous old brick building you’d expect to see in a trendy corner of Brooklyn, and it’s attached to a cheese shop inside what used to be a bank, complete with towering Greek-style pillars.

With summer weather creeping in, the Great Barrington Farmers Market just opened—one of my favorite parts of being up here. My sister picked up seedlings for her garden, while I made a beeline for The little grill to get my usual: a sweet Italian sausage topped with sauerkraut on sourdough. The sun, the smoke coming off the grill, the mix of chatter and dogs and strollers—it all felt like summer had officially clocked in. We even stopped by the Six Depot booth to restock the house with fresh coffee beans.

Another local favorite: One Mercantile. It’s a home goods store with the best selection of candles, incensents, and just the right amount of kitchen stuff that makes you want to host a dinner party even if you live alone.

Last but not least, if you’re ever up this way, I highly recommend heading over to Prairie Whale. Grab a local beer, a genuinely tasty burger, and sprawl out on the lawn. It’s always a scene—especially on Monday nights when there’s a live DJ spinning for the locals.

Great Barrington may be small, but when you know where to look, it’s got a heart of gold.