The Berkshires in October

It’s been a while since I posted a travel blog, as the theme for 2020 has decidedly been stay home. Although Jake and I have missed exploring new places, it’s been equally gratifying to find all sorts of beauty and adventure in our own backyard and out on the farm this year.

We were supposed to get married on September 26, and decided it was best to hold off celebrating with family and friends until next year. We both needed a little honeymoon though, and decided to venture just a little ways outside of the backyard and into the Berkshires. We’ve made lots of journeys out to those hills over the years, but only as day trips and never for an extended stay. So we booked three nights at The Red Lion Inn in Stockbridge, and got excited to explore all of our favorite spots slowly and in their October finest.

The Red Lion Inn is one of my most favorite places in the world. My siblings and I grew up knowing it as a fancy lunch spot with the wooden rocking horse, as my mom and grandmother would take us there around Christmas time. I’d never stayed over though, and was thrilled to experience the historic New England landmark as a guest. I was instantly charmed by the intricate yellow wallpaper in our little room on the second floor, and savored the creaky floors, fireplace, and big old windows looking out to downtown Stockbridge.

Our first hike was a favorite revisited – Steven’s Glen in West Stockbridge. This is a pleasant, easy trail that meanders through an abandoned Christmas tree farm, across the wooded site of many turn-of-the-century jazz parties, and along the bubbling Lenox Mountain Brook. The trail leads to a little observation deck with a stunning perspective of the brook cascading over a ravine. We’d last passed through Steven’s Glen on a very snowy winter day, and it offered a whole new kind of beauty in peak fall foliage.

We wanted to keep dinner casual and outdoors on a still-warm evening, so we picked up pizzas from Berkshire Mountain Bakery and found a picnic spot at Canoe Meadows Wildlife Sanctuary. The pizza was seasonal and excellent – butternut squash, figs, caramelized onions and blue cheese – only to be outdone by the bakery’s famous chocolate chip cookies for dessert.

The next day was devoted to two of our most favorite spots in the Berkshires: Bash Bish Falls and Umpachene Falls. We headed South from the Inn and parked on the New York side of Bash Bish (MA parking lot is closed right now?) and wandered slowly along the stream that leads to the highest waterfall in Massachusetts. No matter how many times we visit Bash Bish, the view always blows us away. It was particularly nice to visit on a weekday, with only a few others hiking, and in peak foliage it felt truly special

Bash Bish always delivers a thrill, but Umpachene Falls is where we go to find a little calm. We make a summertime journey out to this quiet New Marlborough spot each summer for a cool swim, but hadn’t yet made it there this year. It was nice to have the place all to ourselves, and we recalled the first time we went there together and lots of other happy memories as leaves fell into the too-cold swimming hole.

We headed back to the Red Lion Inn beneath foreboding skies, reservations awaiting us in the dining room, and a highly anticipated viewing of the Naumkeag Pumpkin Show to follow. Back in our room, the winds picked up and I watched the Red Lion’s wooden roadside sign fly clean off its post. The rain came down in sheets and thunder hammered, knocking out the town’s power. Here we were, weeks away from Halloween in a spooky old New England Inn, all the lights off; we were elated. We wandered the dark halls and found the lobby glowing with candlelight, the Wednesday night jazz trio carrying on with their show.

As fun as it was, no power meant no fancy dinner and no Pumpkin Show. We shifted dinner plans back South to New Marlborough, where Gedney Farm still had power. We were happy to dine in the place we should have been getting married just a week earlier, and got excited for next year’s celebrations over a delicious meal.

We slept a rather haunted night with no lights and no phones, and awakened to power snapping back on just in time for breakfast. We had sights set over the state line for Friday, heading towards the Catskills and Kaaterskill Falls.

We’d never been to this popular destination before, and the towering, misty cascade certainly lived up to the hype. The winding drive up 23A is breathtaking in October, and the falls themselves are sublime. The trek was a little more populous than we would have liked given the pandemic, but people were pretty courteous about keeping distant and wearing masks.

I insisted we make one stop on our way back to the Berkshires: Rodgers Book Barn in Hillsdale, NY. I’d been following them on Instagram for a while, and I’m never not on the hunt for good second hand books. Deep into country backroads, rolling hills, many cows, and spooky forests, the Book Barn came into view, just as much of a fairytale as I’d hoped. The proprietors were very surprised to see us, as their power was still out, but welcomed us in and offered a flashlight to browse the dark shelves. I loved it all the more.

After reading out on the iconic Red Lion porch for a bit, we enjoyed dinner over in their cozy Widow Bingham’s Tavern. I warmed up with a bowl of butternut squash soup and roasted fall veggies, and Jake had a nice piece of cod. 

Our last day, we enjoyed a perfect breakfast in the dining room, and were thrilled to watch the grand tractor delivery of two giant pumpkins to the Inn’s entrance.

A final hike on our way out was one we’d been meaning to do for years and had never quite found the opportunity: Hollow Fields in Richmond. This is pastoral path mowed into rolling hayfields, leading to forest trails and a beautiful overlook of South County. This was such a pleasant hike on a fall day, and I would love to go back and do it in late spring, when first-cut hay is at full height.

Before heading back East, we stopped at favorite No. Six Depot Roastery & Cafe and split a veggie hummus wrap and lentil sweet potato soup. We have never been disappointed by a meal at this establishment, and once again they offered flavorful twists to old classics that far exceed expectations. I ran into Shaker Mill Books across the street (I can’t resist) and picked up a timely volume of Berkshire ghost stories, and this local cookbook which I’ve heard so much buzz about. 

We returned to our own corner of Western Mass relaxed and refreshed, our case of pandemic wanderlust safely satisfied. There are so many beautiful spots to explore here in our own state, and no better time to do it than October.