A Fall Day in the Berkshires

  • 01 of 14

    Set Out for a Memorable Day of Autumn Adventures in the Berkshires

    Woods Pond Fall Foliage Berkshires Lenox MA
    © 2011 Kim Knox Beckius

    On the Saturday before Columbus Day in 2011, my family and I set out from central Connecticut at 10 a.m. for a day of autumn adventures in the Berkshires: the scenic mountain region in western Massachusetts. On this photo tour, I'll share inspiration and information to help you plan your own memorable Berkshires outing.

    Our first destination--Lenox, Massachusetts--is just an hour east of Albany, two and a half hours west of Boston or three hours north of New York City, so plan your departure time accordingly so you'll arrive in Lenox before noontime.

    Set your GPS for 10 Willow Creek Road, Lenox, MA, and when you arrive and park, you'll be greeted with this spectacular view of fall foliage reflecting in Woods Pond.

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  • 02 of 14

    Reliving the Age of Rail Travel

    Berkshire Scenic Railway - Reliving the Age of Rail Travel
    © 2011 Kim Knox Beckius

    It's time to trade your car for an antiquated form of transportation. When we arrived at the Berkshire Scenic Railway Museum in Lenox, we were impressed by the number of volunteers on hand to point us in the direction of the ticket office, where we purchased passage aboard a leaf peeping train bound for Lee. Check the schedule of fall foliage and Peanuts Great Pumpkin Patch Express train rides offered during the autumn season.

    We opted for the briefest excursion: a 45-minute round-trip ride that departed at 12:15 p.m. While we waited for our train to arrive, we watched old locomotives chugging on the tracks and explored the museum's exhibits, including those showcased inside a Baltimore & Ohio Combine Car, as well as the displays inside the 1903 Lenox Station. My daughter loved observing the interactive model train display. Admission to the museum and exhibits is free.

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  • 03 of 14

    Leaf Peeping from a Train

    Fall Foliage from a Train - Berkshire Scenic Railway Massachusetts
    © 2011 Kim Knox Beckius
    On our fall foliage train ride aboard one of the Berkshire Scenic Railway's vintage trains, vibrant leaves aren't the only things we observed. As the Lee-bound train passed by October Mountain State Forest and abandoned paper mills, we also had the chance to see a blue heron take flight over the Housatonic River and Frog Rock: an painted, frog-shaped boulder.

    While the enthusiasm of the volunteer railroad buffs who operate these scenic rides is admirable, we did find the non-stop narrative a bit much. We assured ourselves that once we began the return trip to Lenox, we'd be able to enjoy a quiet ride... but, we were wrong.

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  • 04 of 14

    Lunch in Stockbridge

    Theresa's Stockbridge Cafe Formerly Alice's Restaurant
    © 2011 Kim Knox Beckius

    Once you've returned to the 21st century, hop in your car and set your GPS for 30 Main Street, Stockbridge, MA. Stockbridge is arguably the prettiest town in the Berkshires, and its strollable Main Street, which inspired artist Norman Rockwell, offers several charming lunch options.

    On-street parking is available but in demand on autumn weekends, but you'll find a spot if you're patient and willing to walk a bit. If you arrive, as we did, around 1:30 p.m., you'll likely be able to find a table, but you may want to have reservations in advance for the most popular dining spot: the venerable Red Lion Inn. If there's no room at the inn, wander down Main Street, and you'll find several other dining options including Main Street Cafe, where we sat at the counter and had delicious soup and sandwiches, or Theresa's Stockbridge Cafe, formerly the Alice's Restaurant famously featured in Arlo Guthrie's song.

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  • 05 of 14

    Apple Picking in the Berkshires

    Apple Picking in the Berkshires - Hilltop Orchards Photo
    © 2011 Kim Knox Beckius

    Once you've enjoyed a leisurely lunch, program your GPS with your next destination: 508 Canaan Road, Richmond, MA. In just over 15 minutes, you will arrive at Hilltop Orchards, one of the Berkshires' most popular places for apple picking. We hadn't yet picked apples this autumn season, so we were anxious to bring a bag home.

    The trees at Hilltop Orchards were loaded with fruit, but we found it incredibly difficult to locate the varieties we prefer: There was no map provided, and signage was poor. Granted, it was a busy holiday weekend, but the staff seemed woefully inadequate to handle the crowd. Be forewarned: You might have quite a wait on autumn weekends if you'd like to sample the orchard's Furnace Brook Wines or if you can't resist the tantalizing aroma of apple crepes being prepared outside. We did appreciate that hayrides to the orchard are free and the apples are priced affordably.

    More Places to Pick Apples in New England

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  • 06 of 14

    Coolest Pumpkin Hayride Ever

    Pumpkin Hayride
    © 2011 Kim Knox Beckius

    We stumbled upon our next destination in the Berkshires somewhat accidentally, but you'll want to be sure to ask your GPS to guide you to 3475 Route 43, Hancock, MA. You'll cross the state line into New York for a portion of this picturesque, 20-minute trip north to Ioka Valley Farm. I'd never heard of the farm, but when I spotted it on a tourist map we'd picked up, I decided we should at least make a quick stop.

    If you're traveling with children, you definitely won't want to miss the farm's agricultural amusements. My daughter and I were dressing a scarecrow when we caught our first glimpse of the hay wagon that takes visitors to the pumpkin patch, and our jaws dropped. With its pumpkin canopy, this hayride was definitely the coolest one we've ever seen: And we've ridden many more hayrides than the average family.

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  • 07 of 14

    A Spectacular Pumpkin Patch

    Pumpkin Patch at Ioka Valley Farm Hancock Massachusetts
    © 2011 Kim Knox Beckius
    Our ride on the pumpkin wagon took us across the street to Ioka Valley Farm's sprawling pumpkin patch, where we found a fine selection of orange orbs. In fact, there were so many attractive selections, the three of us had trouble agreeing on the perfect pumpkin. We finally selected a 37-pound pumpkin that was so hefty, my husband sent our daughter off to fetch a cart: We were impressed that the farm provides them for visitors.
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  • 08 of 14

    Pick Your Own Indian Corn

    Pick Your Own Indian Corn
    © 2011 Kim Knox Beckius
    Ioka Valley Farm also offers the chance to pick your own Indian Corn: a unique activity we'd never previously encountered. According to the posted rules, it's totally cool to peel back the husks to find a mottled color combination that suits your taste. Ears were priced at $1 each as of our 2011 visit.
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  • 09 of 14

    Moonrise Means It's Time to Move On

    Autumn Moonrise in the Berkshires
    © 2011 Kim Knox Beckius

    There was so much more to see and do at Ioka Valley Farm, but when I noticed the moon rising over the autumn-tinted Berkshire hills, I realized we'd better move along if we were going to make our drive's final destination before sunset. We paid for the pumpkin we'd picked and a pre-picked white pumpkin that was the largest we've ever seen, allowed our little girl a couple of quarters to feed the barnyard animals, then hit the road.

    If you are still following along on this tour, you'll want to continue north on Route 43 to Williamstown, then turn right on Route 2 (Main Street).

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  • 10 of 14

    The Mohawk Trail's Hairpin Turn

    Hairpin Turn Mohawk Trail
    © 2011 Kim Knox Beckius

    Proceed west on Route 2, the Mohawk Trail, through North Adams, and you'll soon reach a distinctive, 180-degree bend in the road. This famous Hairpin Turn affords phenomenal views of the Hoosuc Valley and the sculpted Berkshire Hills. Of course, if you are the driver, you'll need to maintain a tight focus on the road as you navigate this dramatic curve. Parking is limited, but we luckily found a spot in the lot near the Golden Eagle Restaurant. If you've worked up an appetite and have time to linger, dinner here may be the perfect end to your Berkshires day.

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  • 11 of 14

    Fading Light

    Dusk in the Berkshires Along the Mohawk Trail
    © 2011 Kim Knox Beckius
    We made it to the Hairpin Turn in Clarksburg, Massachusetts, just in time. The sun was so aflame, I had to avert my gaze as it sank toward the ridge line, casting shadows over the valley below.
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  • 12 of 14

    Fall Colors Shine

    Fall Leaves Berkshires
    © 2011 Kim Knox Beckius
    Even as day turned to dusk, from our vantage point at the Hairpin Turn, we could spy the reds, oranges and yellows of autumnn shining in the twilight. Although fall colors were not yet at peak, they were still impressive to behold on our Columbus Sday weekend drive through the Berkshires.
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  • 13 of 14

    Zooming in on the View

    Hairpin Turn View Mohawk Trail Berkshires
    © 2011 Kim Knox Beckius
    Our eight-year-old is always a big fan of coin-operated binocular tower viewers. The sun was making a rapid descent, so we gave her a quarter so she could zoom in on the vanishing view.
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  • 14 of 14

    The Sun Sets on a Memorable Fall Day

    Berkshires Sunset
    © 2011 Kim Knox Beckius
    It was after 6 p.m., so after we'd admired the sunset sky for a while, we set the GPS for home, pleased with how much we'd seen and done on this single fall day in the Berkshires. After stopping for dinner, we arrived home at 10 p.m.--weary but with wonderful memories of the experiences we'd shared--plus, a bag of apples and two enormous pumpkins.

    If you'd like to extend your time in Massachusetts and have even more fall adventures, be sure to make lodging reservations well in advance, particularly if you're visiting during the busy Columbus Day weekend. Here are suggested Massachusetts Lodgings for Leaf Peepers.