Richmond, Massachusetts, nestled in the heart of the Berkshires, truly comes alive in the late summer and fall. With crisp air, vibrant foliage starting to paint the hillsides, and a relaxed, inviting atmosphere, it’s the perfect destination for a weekend escape. Our regular visits are nothing short of idyllic, filled with delightful experiences that I can’t wait to share.
Start your day at Olivia’s Overlook, a popular scenic viewpoint and trailhead within the 734-acre Yokun Ridge South reserve. It offers expansive views of the Berkshire Mountains, including the Stockbridge Bowl, and is a fantastic spot for both leisurely enjoyment and more active adventures. Visitors can relax at the overlook, which is particularly stunning during sunrise or sunset, or explore the moderate hiking trails that depart from the site, such as the Charcoal Trail and the Burbank Trail, which lead through diverse landscapes and offer additional vistas.
One of the highlights of a Richmond weekend afternoon has undoubtedly become a visit to Balderdash Cellars. Perched on a lovely hill with their grounds overlooking the shimmering expanse of Richmond Pond as the backdrop, this winery offers a truly enchanting setting. Their wines, light and refreshing, are perfect for sipping on a warm late-summer day or a crisp fall afternoon. What makes the experience even better is the rotating cast of fantastic specialty food trucks that park on-site such as Cousins Maine Lobster, La Chalupa y La Enchilada, and Brasato. While you are welcome to bring your own picnic, there’s usually something delicious to pair with your chosen vintage.
But the real magic lies in grabbing one of their Adirondack chairs and finding a spot on the gentle slope that leads down towards Richmond Pond. Here, you can soak in the breathtaking views, while enjoying live music that often graces the air, or even play a game of Bocce Ball on the court alongside one of their buildings. The atmosphere is laid-back and convivial, a perfect blend of relaxation and good company. It’s the kind of place where hours simply melt away as you savor the wine, the food, and the soothing melodies. Be sure to check their website (balderdashcellars.com) for hours, food and music as schedules change weekly.
As autumn deepens, another quintessential Richmond experience beckons: apple picking. Luckily, you’re spoiled for choice in this part of the Berkshires. Both Bartlett’s Orchard and Hilltop Orchards offer the classic fall activity, rows upon rows of trees laden with multiple varieties of juicy, ripe apples just waiting to be plucked. There’s something so satisfying about wandering through the orchard, the crisp air filled with the sweet scent of fruit, and filling your basket with your own hand-picked bounty.
Bartlett’s is a third-generation family owned Orchard and Farm Market that offers not only Apple Picking but an amazing farm stand and bakery. A Bartlett’s, the standout for me is the offering of home-grown vegetables at their farm stand. For example, I’m always blown-away by the tomato selection. Their cider will more than just quench thirst, rather it’s among the best anywhere their baked goods are terrific.
For a slightly different but equally charming experience, consider a visit to the 100yrs old Hilltop Orchard (and now also Furnace Brook Winery). Here, families can also partake in the apple-picking fun, creating lasting memories amidst the picturesque orchard. The winery tasting room offers a casual and enjoyable experience in the middle of an apple orchard. And the real treat? The fresh apple cider doughnuts. Watching them being made and then biting into that first warm, sugary bite is an experience in itself. Warm, perfectly spiced, and utterly addictive, these doughnuts are a must-try and a quintessential taste of fall in the Berkshires.
Whether you’re drawn by the allure a morning hike, lakeside wine and live music, the simple pleasure of picking your own apples, or the irresistible aroma of fresh cider doughnuts, Richmond, MA offers a delightful escape in late summer and fall. It’s a place where you can slow down, savor the beauty of nature, and create cherished memories. So, pack your bags, embrace the changing seasons, and get ready for a weekend of pure Berkshire bliss.
