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.

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.

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.

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.

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

You can download a map of the lake here.

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.

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.

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

You can download and print driving directions here.

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.

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

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.

 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.

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.

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.

The Mount is located at 2 Plunkett Street in Lenox.

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.

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.

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

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.

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.

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

Head here for directions.

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!

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.

Naumkeag is located at 5 Prospect Hill Road in 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!

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

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!

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:

• Most Bewitching Places to Experience Woodstock, Vermont in the Fall
• Where to Experience the Magic of Woodstock, Vermont in Winter
• What to Do on Nantucket to Avoid the 15 Worst Rookie Mistakes
• 10 Fun Things to Do in Kennebunkport
• The Prettiest Lighthouses in Portland for Your Charming Maine Vacation
• The 1-Day Acadia National Park Itinerary You’ll Want to Steal
• Most Instagrammable Towns North of Boston
• 10 Dreamy Gardens in Connecticut You Can’t Miss