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Most Breathtaking Places to Experience Fall in The Berkshires

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Fall in The Berkshires is an experience not to be missed.

After all, I should know. I almost missed it.

Despite the fact that New England’s become my go-to travel region, I was late to hop The Berkshires bandwagon.

I thought I’d completed this year’s Massachusetts “checklist” after recently visiting some towns North of Boston as well as Nantucket.

Plus, I was fortunate to get my foliage fix in Woodstock, so I never envisioned venturing south for autumn amusements.

It wasn’t until I saw fantastic foliage photos on Instagram (after my husband suggested going) that my curiosity was piqued.

While Woodstock in autumn undoubtedly has its charms, I can officially say it’s hard to top fall in The Berkshires.

In fact, I was smitten after just one day trip to this stunning western Massachusetts region.

Since I couldn’t resist sharing these irresistible autumn gems, here are the can’t-miss spots for your Berkshires itinerary.

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A Brief Word on Fall in The Berkshires

The Berkshires are located between two major metropolitan cities, New York and Boston, making for an ideal fall day trip.

However, this beautiful region also offers numerous activities for extended stays, from hiking, to leaf peeping, to cultural events.

Fall is arguably the most beautiful season, with color spilling out over cliff sides, around lakes, and down scenic backroads.

For this reason, the region tends to draw a crowd during this time.

However, with all of the natural wonders to explore and views to capture, you’ll still enjoy peaceful solitude here.

Stunning Sights to See During Fall in The Berkshires

1. Stockbridge Bowl (Stockbridge)

While spending fall in The Berkshires, a visit to Stockbridge Bowl is an absolute must.

This spot is the quintessential autumn lover’s dream.

Stockbridge Bowl – or Lake Mahkeenac, as it’s more formally known – is the largest lake in Stockbridge, Massachusetts. This manmade body of water runs nearly two miles long and is a popular launch point for boaters and watersports enthusiasts.

It also offers a public beach for swimmers and lake dwellers to enjoy in the warmer months.

You’ll likely see a number of boats drift by and/or enter the water through the boat launch while you’re here.

PHOTO TIP: Stockbridge Bowl makes an absolutely stunning backdrop for your fall photos. Whether you’re sailing the lake or enjoying the view from shore, don’t miss a chance to capture autumn’s unique beauty.

Since this lakeside area is quite expansive, I suggest using a telephoto lens (70 – 300mm) to capture more tree detail. Unfortunately, much of the stunning color will be lost with a shorter focal length.

In addition, on a relatively still day, you can capture the mirror-like reflection in the water, as we did above.

However, this will unfortunately be unlikely (or impossible) on a windier day, as wind creates a ripple effect in water.

For instance, as you can see below, we lost the reflection once the wind picked up here.

What to Know Before You Go:

Stockbridge Bowl is open to the public year-round.

Access to this spot is free and there’s a parking lot conveniently located in front of the water access point.

How to Get Here:

The address of the Stockbridge Bowl Boat Launch is 106 Interlaken Road in Stockbridge. 

You can download a map of the lake here.

2. Norman Rockwell Museum (Stockbridge)

Be sure to pay a visit to Norman Rockwell Museum while in Stockbridge.

This famous museum was founded in 1969 to honor Norman Rockwell’s American illustrations and societal contributions. It’s the largest Rockwell collection in the world.

In addition to fascinating year-round exhibits, the museum sits on a plot of land that’s simply stunning in the fall.

FUN FACT: Rockwell resided in Stockbridge for the final 25 years of his life. Although he occupied around 20 art studios throughout his career, he left his last to Norman Rockwell Museum in 1976. The building was eventually divided into two parts and relocated from his backyard to the Museum’s grounds in 1986.

The public can view Rockwell’s original art materials and personal belongings within the studio from May to October.

PHOTO TIP: Head down the hill across from Rockwell’s studio to capture the stunning foliage behind it.

In addition to photographing his iconic studio, be sure to capture Linwood Estate behind it on the hill.

What to Know Before You Go:

While the grounds are free to visit, you’ll need to pay to gain entry into the museum. 

Keep in mind that the museum requires you to purchase tickets in advance for pre-determined time slots. Head here for visiting hours and admission rates.

How to Get Here:

Norman Rockwell Museum is located at 9 Glendale Road/Route 183 in Stockbridge.

You can download and print driving directions here.

3. Santarella Gingerbread House (Tyringham)

I first discovered Santarella in a YouTube video about The Berkshires and was immediately intrigued.

This fascinating property dates back to 1739 and is affectionately known as the Tyringham Gingerbread House.

Without exaggeration, this enchanting place looks as though it was taken straight out of Grimms’ Fairy Tales.

It looks especially pretty in the fall, as the property is covered in a veil of foliage.

FUN FACT: Santarella’s most notable resident was Sir Henry Hudson Kitsen, a famous English sculptor.

You can read more about the property’s interesting history here.

PHOTO TIP: Unfortunately, Santarella is a private property, so you won’t be able to access it beyond the fence. This can make photography a bit of a challenge.

You’ll have to get a bit creative and shoot at an angle to avoid the yellow chain barrier that ropes off the entranceway.

I recommend shooting with a wide angle lens (35mm or less), as your photographer will need to get pretty close.

What to Know Before You Go:

Although the property’s private, this 4-bedroom fairytale dream home is available to rent for special events or a Berkshires getaway.

Alternatively, you can quickly park in the lot in front of the fence if you’re just swinging by for a quick picture. Try not to linger too long and don’t go beyond the fence.

How to Get Here:

 Santarella is located at 75 Main Road in Tyringham.

 It’s just two hours from Boston and two and a half hours from New York City.

4. The Mount (Lenox)

While spending fall in The Berkshires, head into Lenox to visit The Mount.

This National Historic Landmark and cultural center is the former country estate of literary legend Edith Wharton.

This famous American author designed and built this impressive turn-of-the-century home in 1902.

In addition to a beautiful property and grounds, The Mount offers year-round artistic and literary programs as well as school tours.

You can read about the history of the estate and its literary legend here.

PHOTO TIP: Although we didn’t explore the grounds in depth, there’s a path of trees leading up to the property that’s perfect for fall photos.

You may also be able to capture beautiful foliage surrounding the property if you hit it at the right time.

What to Know Before You Go:

The grounds are open daily. Although advance reservations are required for the Main House, you don’t need them to walk the grounds or visit the bookstore.

However, I suggest calling ahead before your visit, even if you’re only intending to walk the grounds.

Much to our surprise, there was an admission booth set up in the parking lot when we arrived. While I’m not entirely sure about the procedure for walk-ins, there did appear to be a general entrance fee. I recommend inquiring about this in advance so you’re prepared for all scenarios.

Head here for contact information, visiting hours, and admission rates for the Main House.

How to Get Here:

The Mount is located at 2 Plunkett Street in Lenox.

5. Mount Sugarloaf State Reservation (South Deerfield)

Mount Sugarloaf State Reservation is a must-see in autumn, particularly if you’d like to view the gorgeous foliage from above.

The summit offers a breathtaking birds-eye view of the Connecticut River Valley.

What to Know Before You Go:

Although there’s an auto road leading up to the summit, it’s closed for the season and won’t reopen until spring 2021.

However, visitors can still hike up to the top. Fortunately, the hike only takes about 20 minutes each way and is relatively short.

That said, it’s quite steep in spots, so wear adequate footwear.

PHOTO TIP: While the view is undoubtedly beautiful here, you’ll likely run into a few photo hiccups at this location.

The most disappointing part about this viewpoint is the unsightly chain link fence surrounding it. Unfortunately, the fence makes it difficult/impossible to shoot anything other than landscape photos here.

In addition, the lookout tower was closed for construction when we arrived, making it difficult to shoot an alternate angle. I imagine the tower will be accessible again to visitors come spring, but be prepared, just in case.

Your best bet is to stand against the fence while shooting to keep it out of your shots.

How to Get Here:

Mount Sugarloaf State Reservation is located at 300 Sugarloaf Street in South Deerfield.

6. Hilltop Orchards & Furnace Brook Winery (Richmond)

If you’re hoping to cash in on the fruits of the season, be sure to stop by Hilltop Orchards & Furnace Brook Winery.

This 200-acre orchard/winery offers seasonal apple picking, a farm winery store, and fantastic hilltop views.

In addition, the beautiful property also offers wine tastings under normal circumstances, but those have ceased until further notice.

What to Know Before You Go:

The property is open daily from 9AM – 5PM year-round.

In addition to their tasty offerings, they also have a variety of hiking trails for all abilities.

How to Get Here:

Hilltop Orchards is located at 508 Canaan Road/Road 295 in Richmond.

Head here for directions.

7. Naumkeag (Stockbridge)

I first discovered stunning Naumkeag online and was curious about visiting.

This stunning Gilded Age Mansion and former estate sits on an impressive 48-acre property. Its known for its unique architecture, magnificent gardens, and Berkshire cottage.

There are also seasonal events such as The Incredible Naumkeag Pumpkin Show, where the gardens are transformed into a festival of jack-o-lantern lights.

Although we didn’t make it here this year, it’s definitely on my radar for a future visit.

Fortunately, if you miss it as well, you can check out Winterlights –  their brilliant festival of holiday lights – instead!

What to Know Before You Go:

Whether you’re attending an event or touring the grounds, you’ll need to plan ahead and book your visit in advance.

Unfortunately, we learned this the hard way. We were hoping to walk in and explore the grounds, but the gate was closed.

However, if you have the luxury of time, I highly recommend planning a visit here.

How to Get Here:

Naumkeag is located at 5 Prospect Hill Road in Stockbridge.

Where to Stay During Fall in The Berkshires

The Red Lion Inn (Stockbridge)

As you may have gathered, Stockbridge is one of the most beautiful and popular towns in The Berkshires.

I recommend booking a stay at the iconic Red Lion Inn if you’re planning to stay in the Stockbridge area.

This quintessential Berkshires property offers four distinct lodging styles. Guests can stay at the Main Inn or Maple Glenn, the Village Houses, or in their unique, twentieth-century converted firehouse.

While my husband and I haven’t stayed here ourselves, multiple family members recommended it to us.

Regardless, it’s absolutely worth driving by to admire the beautiful fall decor, even if you’re not spending the night.

It’s simply gourd-geous this time of year!

How to Get Here:

The Red Lion Inn is located at 30 Main Street in Stockbridge.

33 Main (Lenox)

Alternatively, for more of a walking town, consider a stay at 33 Main in Lenox.

This latest Lenox property combines traditional bed-and-breakfast charm with the modern amenities of a luxury hotel.

They also have some festive décor if you’re looking for a pretty photo backdrop!

How to Get Here:

33 Main is fittingly located at 33 Main Street in Lenox.

I hope this guide has given you plenty of autumn inspiration for your trip to The Berkshires. This scenic region was a literal breath of fresh air and I’m already dreaming of my return…

Have you ever experienced fall in The Berkshires? What were some of your favorite spots? Let me know in the comments; I’d love some fresh inspiration for a future trip!

Also, if you’re looking for additional New England resources, be sure to check out my other area guides:

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38 thoughts on “Most Breathtaking Places to Experience Fall in The Berkshires

  1. I love the Berkshires and just spent a weekend in Williamstown and North Adams area. Stockbridge is on my list and will definitely be my next Berkshires destinations. Love all the photo tips!

    1. Ahh, very cool, small world! Stockbridge is definitely one of my favorite towns there, so I highly recommend basing yourself there. So glad you liked the photo tips!

  2. Gorgeous photos, and such great tips. I absolutely love the gingerbread house. It’s the perfect creepy but adorable fall looking house. And really nice reminder that we don’t need to trespass to get good photos

  3. Your photos are stunning!! I have yet to get to the Berkshires surprisingly, but your post makes me wish I went for the foliage! The Santarella Gingerbread House looks so cute!! Thank you for sharing these helpful tips! I’m going to save this post for when I visit next year. 🙂

  4. I haven’t heard about it before seeing your photos on Instagram and I was so amazed! I love the colors, the location between NYC and Boston seems ideal, and last but not least the houses you shared are so picturesque!

  5. Beautiful as always! Obviously, my favorite spot is the Tyringham Gingerbread house. I wish we had those fall colors in Israel, but in the meantime, I’ll drool over your photos.

  6. Wow all of these locations look absolutely amazing with the fall colours! It’s my favourite time of the year and your photos are making me want to go here!

  7. Your photos are stunning! I had no idea there was a Norman Rockwell museum. I would love to see that, my Granny has a lot of Norman Rockwell prints in her house and it makes me think of her. The Gingerbread house is so cute, I would love to see that as well. Thanks for sharing 🙂

  8. These places are all so beautiful. However, I have to admit the Gingerbread House was my favorite from the list. I found the Red Lion Inn super cute too.

  9. I love how you are always discovering amazing places that I never heard of before – this place is magical, especially during fall! The Santarella Gingerbread House is incredible, as well as your pictures. Adding Berkshires to my list of must-visit places for next time I am around Boston or NYC. Thanks!

  10. This place looks amazing! I love all your pictures and recommendations 🙂 Your blog posts make me want to explore more the USA when I get the chance. I’m saving this for future trips.

  11. Wow! The Berkshires truly does look magical in the fall. I was really considering doing a last minute fall trip there before Thanksgiving, but I decided on the Finger Lakes instead. I’m definitely making it my mission to do this trip as well as Woodstock next fall. 🙂 Your photos are gorgeous and I love your outfits.

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