Whether you live in the area or are just passing through, we’re sure we can all agree: there’s nothing quite like fall in Berkshire County. The explosion of colors, fresh New England apples, and cool evenings made for cozy sweaters and warm drinks...what’s not to love?!
Here at All Seasons Realty Group, fall is a special time filled with memory-making opportunities everyone looks forward to all year long. And we want to share our top 5 fall activities with you!
- Apple Picking
Unless you’re blessed with your own backyard orchard (and yes...we’re jealous), it’s been a hot minute since you’ve bitten into an apple straight from the tree. No offense to our local grocery stores, but...daaang. The crisp, sweet-tart bite of a freshly picked apple can’t be beat. Plus, most orchards offer far more than just apple picking, making it an ideal activity for the entire family.
Our top Berkshire apple orchard picks include:
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Jaeschke’s Orchard--Adams, MA
You’ll know why this third-generation family-owned orchard is a top pick the moment you turn into the driveway. These views are seriously Instagram-worthy. Mt. Greylock, the highest point in our fair state of Massachusetts, towers in the background and creates a truly special setting for your outing. Grab a snack from the farm store (or your bag of freshly-picked heirloom apples!), relax on the picnic tables, and take in the view.
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Bartlett’s Orchard--Richmond, MA
There’s a strong and ongoing debate on who has the best cider donuts in Berkshire County, but for us, there’s no place like Bartlett’s. A warm sugar-coated donut paired with a glass of their own freshly-pressed cider feels like a little piece of fabulous fall heaven. Plus, their store is chock full of fun and interesting local products, and the orchard a pristine apple-picking dream.
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Lakeview Orchard--Lanesborough, MA
A beautiful orchard nestled in the Berkshire Hills, this hidden gem guarantees a picturesque apple picking experience. Not only that, but their farm stand offers their own produce and a variety of homemade pastries, jams and jellies, cider and more!
- Hiking
Don’t get us wrong, we’re down for a hike almost any time, anywhere. But during the height of summertime humidity, the thought of working our sweaty way up a mountain is definitely less than enticing. Fall is the perfect time for hiking--bugs are practically nonexistent, it’s warm but not too warm, and the extravagant autumn views and colors will blow your mind.
Some of our favorite places to hike include:
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Greylock Glen--Adams, MA
So…remember that orchard with the crazy views of Mt. Greylock? Jaeschke’s? Consider your day made by combining a trip to the orchard with a hike at Greylock Glen, a mere 0.3 miles from Jaeschke’s itself. This location boasts 26 trails of varying lengths and degrees of intensity. Whether you’re looking for a casual stroll through their groomed walking paths or a classic trek into the woods, the Glen offers something for everyone. Check out their site for a printable map and trail descriptions!
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Cheshire
Cobbles--Cheshire, MA
Want some serious bang for your metaphorical buck? Then hit up the Cheshire Cobbles trail. There are two separate entrances, but no matter which way you choose it’s still only about a mile to the top, where you are treated to one of the best outlooks in Berkshire County. Once the rich fall colors set in, the views showcasing Cheshire Lake, Mt. Greylock, and the surrounding Berkshire hills are especially spectacular.
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Monument Mountain--Great Barrington, MA
Monument Mountain is another popular hiking spot with gorgeous sights and rich history. In 1850, Herman Melville and Nathaniel Hawthorne hiked up the mountain together and got caught in a thunderstorm (wouldn’t be the Berkshires without some cray-cray weather), and it was the location that inspired William Cullen Bryant’s poem, “Monument Mountain,” a macabre tale of forbidden love and death just right for the month of October.
- Pumpkins!
‘Tis the season for PUMPKIN EVERYTHING, and that goes way beyond purchasing a pumpkin spice latte at Starbucks (but...go do that, too). A bright orange field of pumpkins awaiting selection is a sure sign of fall, and the perfect activity to include in your autumn bucket list.
If you’ve ever driven through Cheshire on Route 8 during the fall, you know exactly how exciting the pumpkin festivities can be. Every weekend during the month of October, Pumpkin Fest rages at Whitney’s Farm in Cheshire, MA. Not only do they have loads of pumpkins to choose from, but they also have a host of activities particularly suitable for family fun, including local vendors, bouncy houses, a giant slide, haunted corn maze and pony rides. Trust us, this place has all the makings of a new family tradition!
The Incredible Naumkeag Pumpkin Show is another beautiful celebration of fall that you won’t want to miss! This is a ticketed event and purchase is required ahead of time (no on-site ticket sales) so snatch those up now and mark your calendar! The thousands of hand-carved pumpkins on display are a dazzling tribute to the season and Berkshire creativity.
- Ramblefest and the Greylock Ramble--Adams, MA
The fall festivities continue with Ramblefest and the Greylock Ramble, coming up this Columbus Day weekend! Join the Berkshire community at the Adams Visitor Center on Sunday for an exciting street festival featuring local craft beer and wine, live music, great food, and a variety of vendors and activities.
Come back Monday morning to catch a shuttle that will bring you to the base of the Cheshire Harbor Trail, and join the hundreds of locals and visitors alike in a trek to the summit of Mt. Greylock. This adventure is not for the faint of heart, as the 6.6-mile round-trip trail can be strenuous, but for those willing to take on the mountain, this is an experience you won’t forget. Pro tip? Pack a hearty lunch and wear layers--you might need them at the top!
- Chocolate Springs--Lenox, MA
While all these wild fall activities are a blast, we can’t ignore the fact that sometimes we just want to wrap ourselves in scarves and our favorite flannels and indulge in an outing that caters to the cozy, quiet side of fall. So it’s only fitting that we end this post on a decadent note...and it doesn’t get more decadent than Chocolate Springs. This local establishment and its luxurious chocolatey creations have been featured in magazines such as Time Magazine and The New York Times, and are well-deserving of every accolade. Whether you choose a rich homemade dessert or a steaming cup of the best hot chocolate on the planet, a trip to Chocolate Springs is a warm, comforting haven perfect for a chilly fall day.
So What
Are You Waiting For?
This season won’t last forever, but winter will sure feel like it does...so get outside, soak up the sunshine and make the most of these beautiful Berkshire fall days!
