If you have “friends” in the Berkshires on Facebook, no doubt you’ve “liked” more than one stunning picture taken from Olivia’s Lookout (about 1.5 miles up Lenox Rd from the turn off of Rt 183/West St in Lenox). It’s the perfect spot to kick-off your Richmond Road Trip and to stop for some panoramic leaf peeping overlooking Stockbridge Bowl and Gould Meadows.
From the Lookout parking area you can easily hop on Burbank Trail, a 3.2-mile loop that circles Monks Pond and the 1850’s Gorman Homestead. The Yukon Ridge South trailhead is also just across Lenox Rd. Other nearby hiking trails include Yukon Ridge North, Yukon Ridge South, Burbank Trail, Charcoal Trail and the Micheal H. Walsh Trail.
But, if you’re hiking with kids, I strongly recommend jumping back in the car for a drive past SHARK ROCK! It will be just up the road on your right as you head away from the Lookout, toward Richmond.
Then keep an eye out for a sharp left turn onto Stevens Glen Rd, where you will spot Natural Resource Council signage, a small parking area and the nearby trail map.
Stevens Glen offers 128 acres of family-friendly hiking trails featuring wild blackberry bushes, natural stone steps, rustic benches and bridges, an observation deck, and magnificent views of gorges, glens and the cascading falls of the Lenox Mountain Brook.
After your hike, set your GPS for 508 Canaan Rd/Rt 295 in Richmond, for apple picking, cider donuts and free hay rides at Hilltop Orchards, and a sip (or two) of Furnace Brook Winery’s award-wining wine or hard ciders. (The first one is free and guests are welcome to try five more for just $5.) Visitors are also more than welcome to explore the full 200-acre property and hike the professionally designed Johnny Mash I & II Trails (3.2 miles).
Another equally delicious and family-friendly option in Richmond is Barlett’s Orchards (575 Swamp Rd) —a local farm specializing in apples and produce, with a country store brimming with fresh baked cider donuts, ginormous apple muffins, pies, turnovers, and an assortment of seasonal goodies and staple items, plus, pick your own apples, raspberries, and flowers, every weekend from Labor Day to Columbus Day.