Early this September, Denny and I began traveling further and further north in search of autumn. Though we’d had a great summer, those first 60 degree days had us craving cooler temperatures and magical autumn hikes with colorful foliage. Though our go-to is the Catskills, for this adventure, we needed to venture further north–and in this case, east–to find a place where autumn was beginning. We landed on a visit to the Berkshires, just over the three hour mark from NYC.

What we found there were massive pines, huge waterfalls and low rolling mountains. We stayed overnight in the super-cozy Briarcliff Motel, just far enough away from the nearest city of Great Barrington to make it feel like we were really “out there.” The vibe at Briarcliff Motel is very easy-going, the decor simple and contemporary meets outdoorsy, without being at all pretentious. The motel was busy, and we were surprised to see that many of the other guests were vacationing Europeans, here to see the autumnal change in the Berkshires.

In the early evening, we enjoyed the firepit on premises that overlooked the massive Monument Mountain, which loomed across the street from the motel. (More on Monument Mountain below, which you should definitely take advantage of during your stay!) During morning hours, we chatted with the owners while grazing on the buffet-style breakfast spread using ingredients from local farms. The owners, Richard and Clare, are Europeans who came to the Berkshires to live their dream in the Northeast. Aside from being motel owners, they are downright lovely people who are more than happy to help you with recommendations of where to hike, hang out, and eat in the Berkshires. You know–if you can’t find what you’re looking for below!

What to Do in the Berkshires: Hike a Mountain, Explore a Waterfall, and Take the Long (Scenic) Way Home

Wanting to experience as much of the outdoors as possible, we went on three separate hikes while we were visiting the Berkshires. We were first drawn to Ice Glen as soon as we heard its name; early fall had given us a 75º day and we wanted to hike a trail we wouldn’t overheat on. We’d heard about this trail that cools down about 15 degrees inside a glacial ravine, where its massive boulders’ nooks and crannies are known to harbor ice and snow well into the summer. At the south end of the ravine, the trail also leads hikers to the tallest pine tree in Massachusetts. The hike is only moderately difficult; it’s a bit of a climb, but also pretty short, clocking in at about an hour. Ice Glen’s trailhead begins at the foot of a wooden bridge, then passes over some long forgotten railroad tracks before the 600 foot ascent. After the climb, an opening in the thick forest gives way to the stacks and clusters of enormous boulders in this magical glacial ravine.

The second hike we did was at Bash Bish Falls State Park, the biggest waterfall in the entire state of Massachusetts. To our surprise, the hike–if it could even be called that–was more like a leisurely stroll along a creek for 20 minutes. Since it had stormed, colorful autumn leaves covered the forest floor. The creek, fed by the massive waterfall, was gushing and made for a lovely soundtrack to our quintessentially autumn afternoon.

We also hiked Monument Mountain, whose trailhead parking lot is almost directly across the street from the Briarcliff Motel. (Pro tip: walk to the trailhead–you have to pay to park here!) It’s about an hour to the top, whose 360º views of the area are great.

Last, on your way home, make sure to take the very scenic Route 7. We could barely go a mile without pulling over to take in the mountain views, the sweeping vistas and meadows, century-old barns, and of course, lots of farm animals. We also stopped at a couple farm stands along the way, stocking up on fresh eggs, cheese, jams, and tomatoes to bring back to the city.

Where to Eat and Drink in the Berkshires

Our most memorable dining experience is tucked far into the woods of the Berkshires at the Dreamaway Lodge, a restaurant and bar describing itself as “an atmosphere long remembered.” The colorful establishment is housed in a 200 year old farmhouse, lit with neon signs, Christmas lights and antique table lamps. They book live entertainment often, providing some much-needed entertainment and/or creative outlet for locals–on the night we visited, an open-mic turned into a full-out jam session. We enjoyed dinner at our table, checked out the band, then joined some friends by the outdoor firepit with hot toddies in hand.

We also loved Nudel, serving up seasonally inspired food with a focus on pasta. We bellied up to their bar, where we watched Chef Bjorn Somlo create our dishes right before our eyes. Make a reservation or go on the later side to try and snag the bar seats, of which there are only five or six. Though we didn’t get to try it, we heard great things about Prairie Whale, where Brooklyn restaurant pioneer Mark Firth brings the same quality food he served as his previous restaurants Marlow & Sons and Diner. The menu changes daily, using the freshest possible produce and meats.

For lunch, we enjoyed Barrington Brewery where beer is brewed using 100% solar power. They serve totally standard pub fare, but their beers are pretty solid getting an average of 87% on Beer Advocate. The space feels almost cabin-like, with huge wood booths and Adirondack-style decor. Weather and season permitting, The Bistro Box is the top pick in town for lunch. It’s a roadside cafe owned by New York’s own Culinary Institute of the Arts in the Hudson Valley. Visitors take their food to-go, or enjoy on their picnic tables. (Open May through November.) We also enjoyed stopping in for coffee at the beautiful Rubi’s–sister-cafe to cheese shop Rubiner’s–which is housed in an old bank. The cafe serves specialty sandwiches, keeping it to simple cheese-friendly recipes like grilled cheese, cubans, and ham & cheese.

Last, we really enjoyed visiting Moe’s Tavern whose website’s url says it all: NoCoorsLight.com. Expect not only a great craft beer selection, but also a huge variety of whiskeys and bourbons. We’re not really sports people, but we did love this sports bar to try some of the areas local beers. Around the corner, they have a to-go store called Trader Moe’s. We made a night of first hitting the bar and then the store for some beers to enjoy at the hotel. Cheers!