October 2024
A Weekend with Fall Foliage in the Berkshires, Massachusetts
After an incredible summer of travel, I had not given much thought on how to spend my birthday trip. Since flights were still expensive and our time was limited to a four day span, I looked around at drive-able destinations. We had such a spectacular trip to the White Mountains in New Hampshire so I looked at other New England fall foliage areas and found the Berkshires in western Massachusetts with plenty of small towns to explore. I found a fall foliage tracker and first, could not believe this was a thing and second, was pleased to find that during the second weekend of October, we were in peak fall foliage – The Berkshires, here we come! Consider us leaf peepers for the weekend.
We drove up after work and checked in to our beautiful Airbnb. We picked staying near Pittsfield since it was central to the western Berkshires area we wanted to explore, and would say saying near Lenox is another good choice. This Airbnb is a loft unit on Bittersweet Farm – they even have a farm stand where you can purchase farm products such as produce, flowers, and eggs – and enjoy the animals on the farm like chickens, goats, and horses. We adored our stay here and it worked perfectly for our Berkshires itinerary. After settling in, we promptly went to bed ready to start our exploring in the morning.
Day 1
As the sun peeked over the mountains, we could see the fall colors beginning to shine. Our first stop was breakfast at a spot around the corner, Flo’s Diner. Open for breakfast and lunch, the local stop serves up traditional diner menu favorites. We both ordered eggs, hash browns, toast, and bacon to fuel up for the day. This spot is certainly one we recommend if you need a breakfast or lunch spot in the area.
Ready for fall foliage sightings, we made our way to Monument Mountain Reservation to hike the Hickey and Peeskawso Peak Trail.
Read about the Hickey and Peeskawso Peak Trail at Monument Mountain Reservation here!
After a beautiful and relaxing hike, we were ready to explore the nearby farms and towns to experience more fall activities. Nearby, Taft Farm was blossoming with fall. Outside were countless pumpkins, mums, and other fall plants. Insider is a full market with farm grown produce, farm made products like jam, a deli for sandwiches, freshly made baked items including cider donuts, and a full plant nursery. We were here for the cider donuts so we grabbed two and Kevin grabbed a ginger snap cookie as well. I really loved these donuts, very classic cider donuts presentation, and I think it was my favorite of the trip. Outside, there is a flower garden, farm animals, and a full corn maze themed this year to Ghostbusters, all of which we really enjoyed. Taft Farms was a great first farm stop of the trip!
Ready for coffee number two of the day, we stopped into the small town of Stockbridge at at Stockbridge Coffee and Tea, which also features a small bookshop – one of our favorite additions to a coffee shop. We walked briefly around the downtown before hopping back in the car for a stop I was extremely excited about.
Nothing brings me quite the delightful excitement like a full dairy farm – cheese and ice cream are some of my favorite foods. So when I found High Lawn Farm, there was no question this was a mandatory stop on our trip. But I do not think I was prepared for just how wonderful this place is, so much so, it is getting a dedicated blog post.
Read about visiting High Lawn Farm here!
I saw many itineraries include the Norman Rockwell Museum and while it was well rated, I was not expecting to spend time inside a museum – I also did not recognize who Norman Rockwell was. But when Kevin noticed a sign for it declaring recognition, I looked again and realized I did in fact know this guy, I just didn’t put together the name with his work. We had some time in the day so we swung into the Norman Rockwell Museum.
Is it worth the stop? Read about our time at the Norman Rockwell Museum here!
On our way back to the Airbnb to get ready for our evening, we stopped at another farm – for science of course – how else would we be able to determine the best in the area? Barlett’s Orchard Farm Market is a generously sized store with freshly baked items, including cider donuts, plenty of apples including the option to pick-you-own apples, and farm made items like jams and maple syrup. After grabbing cider donuts, we spotted freshly ground peanut butter which ended up being such a treat – we never had peanut butter this fresh and pure, highly recommend! The cider donuts here are different from the first ones we had today. These were more of a spiced version and Kevin really enjoyed these.
After freshening up at the Airbnb, we headed out to downtown Lenox. With time to spend before our dinner reservation, we walked around and stopped into some of the shops. We first visited The Bookstore and Get Lit Wine Bar – a bookstore with a wine bar? Match made in heaven. We overheard the owner explaining to other patrons that this bookstore was featured in a movie for their efforts during COVID to stay open. We then hopped next door to Dare Bottleshop & Provisions which we definitely needed more time to enjoy fully.
Around the corner was Cello where we had reservations tonight. The excellent reviews instantly added this to our dinner list
Read our full dining review for Cello here!
Day 2
Our second day in the Berkshires took us north to explore the areas of Cheshire and Adams / North Adams. There is tons going on north of Pittsfield and wanted to see how much we could squeeze into this mini-road trip. Though I have to say, waking up to this view every morning was such a treat.
The first stop on our journey was for breakfast at the Daily Grind. The reviews here were great but when we walked in, it certainly was not what I expected. That is not a bad thing but I guess based on what I read I anticipated a coffee cafe but this was a hole-in-the-wall, no nonsense, cash only, local jaunt through and through. We love stumbling upon *the* place where people in town end up each morning and everyone knows everyone. The food menu here is typical breakfast fare, we shared a burrito as the portions here are very generous. A great way to start our day.
I had a few short hikes highlighted for the day, the first being the Cobbles Trail. I have to say, information for this trail was not great but I had enough detail that I knew it existed. And while it was very tough to find, this short trail along the Appalachian Trail is a hidden gem.
Read about the Cobbles Trail along with how to find it here!
After this spectacular fall hike, we traveled further north to Natural Bridge State Park. In my research, this spot reminded me of Watkins Glen in the Finger Lakes in that it is a natural gorge that has trails that allow guests to walk along and within it so we were looking forward to this next stop.
Read about the Natural Bridge State Park and if it is worth a visit here!
We parked in downtown North Adams to explore this town as it was bopping. Our first stop was a collab area by the MOMA. While we did not visit the MOMA on this trip, it is a very well rated museum so definitely consider it if this interests you. With a bunch of stores in this area, we stopped in Tunnel City Coffee for Kevin’s second coffee. Tunnel roasts their own coffee and the warehouse vibes here are relaxed – definitely a great stop for your coffee fix.
We bopped in and out of a few stores, including Berkshire Emporium and Antiques (there is an entire antique route you can travel throughout the Berkshires if you are into antiquing!) and the Bear and Bee Books – the downtown North Adams area definitely deserves some time to explore.
The most well rated place for a bite to eat is Jack’s Hot Dog Stand. It made no sense to me so I knew we had to try it. Inside is a counter with seating for less than a dozen people and a few staff behind the counter grabbing orders and moving the crowd along. This is clearly a spot that both locals and tourists alike come too and there does not seem to be judgement in either direction. The menu is simple and cash only – a simple, plain hot dog is $1.95 – WILD. They also have some toppings like cheese and chili, burgers, and some fried options like chicken and fries. Kevin and I each got a plain hot dog and Kevin also ordered a chili hot dog. The hot dogs are small so it is easy for someone to come in and get five of these no problem. But at this price point? So great. I also read a comment about the chocolate milk, and while random, I did see someone seated with his hot dogs and a giant thing of chocolate milk. And yes, it was absolutely delicious and a must order along with your hot dog fix. Not that I did not believe the reviews, but boy they were right. Even for a small snack, it is worth visiting this establishment when in North Adams.
Moving along with our day, we decided to skip the Cascades Trail and instead make the drive to the top of Mount Greylock.
Read about visiting the top of Mount Greylock here!
One our way back to Pittsfield, we stopped at Whitney’s Farm where it was covered in fall festivities. Our first order of business was to try their cider donuts which were classic and delightful. The farm featured a petting zoo, trailer rides, kids activities, and hundreds of pumpkins to choose from. The fall game at the farms in the Berkshires was so epic!
We returned to the Airbnb to get ready for dinner which took us back to Lenox. While we scrambled a bit to find a place to eat after ditching my pre-vetted plans but we certainly were happy to be returning to Lenox and snagging a very last minute reservation at Bistro Zinc.
Read our full dining review for Bistro Zinc here!
Day 3
Our final full day in the Berkshires and I had a jam packed day planned. But before all the plans, we made our way to downtown Pittsfield for breakfast at Dottie’s Coffee Lounge which was absolutely exceptional – I cannot recommend this spot enough.
Our first stop of the day was the Mass Audubon Pleasant Valley Wildlife Sanctuary. You know we are always up for the opportunity to bird watch and with fall foliage built in, this seemed like a win-win visit.
Read about our visit to the Mass Audubon Pleasant Valley Wildlife Sanctuary here!
Ready for coffee number two, we made our way to West Stockbridge to the very popular No. Six Depot Roastery & Cafe. I think we waited almost a half hour for Kevin’s coffee – their efficiency could certainly be improved a bit since it is clearly a crowded location but it was a good beverage. From there, we popped across the street to Shaker Mill Books which clearly was going to require more than a few minutes of time. We bookmarked the shop for later in the day if we had time – really all of West Stockbridge deserved more time to explore so we were hopeful to come back.
Fall festivities are abundant throughout the Berkshires and the weekend we visited was the Harvest Festival at the Berkshire Botanical Gardens.
Read about our time at the Harvest festival at the Berkshire Botanical Gardens here!
After a great time at the Harvest Festival, we made the easy decision to return back to West Stockbridge to continue exploring. There are so many great shops and would like to highlight a few that you have to visit. Charles H. Baldwin & Sons has been in operation since 1888! Specializing in extracts, their pure vanilla extract is famous and it is simply magical in this store. We made quite a number of baking purchases here both for ourselves and as gifts. Ella May’s has great ice cream – not that we were hungry but we could not pass it up, especially when locals doubled down by telling us how good the ice cream is here and indeed, it is quite delicious. And then we returned to Shaker Mill Books – there are so many books so Kevin was in heaven. We were so impressed with West Stockbridge and it was definitely one of our favorite spots of the trip.
Before our evening activity, I had the perfect spot in mind for dinner and I dare say it is one of the best hidden gems of the Berkshires. Baldwin Farms was just a short distance down the road and while this spot is not like the other farms that were overrun with fall festivities, Baldwin Farm focuses on the literal definition of farm to table. They have an indoor farm stand with all their products including various meats, eggs dairy products and more. I wish we had a cooler to have bought up a bunch of their items. But we were really here for the food truck. Using meat raised on the farm, this food truck is serving up absolutely incredible sandwiches including smash burgers, fried chicken, pulled pork, and more. Kevin and I both got a sandwich – fried chicken and pulled pork – and wow, what fantastic sandwiches. Absolutely get here when visiting the Berkshires!
One fall activity that definitely sold me on a trip to the Berkshires was finding The Incredible Naumkeag Pumpkin Show. I have seen pumpkin displays advertised in the past but have never had the opportunity to attend one. This would be the perfect time to check that off the fall activity list. The tickets were a bit expensive so I was a bit concerned that this was a money grab but I remained optimistic.
Read about our evening at The Incredible Naumkeag Pumpkin Show and if it was worth it here!
Day 4
Our final morning before the long drive home but not before a few more stops in the Berkshires. We went back to Dottie’s Coffee Lounge as we had such a lovely breakfast there yesterday and Sunday morning’s featured a jazz brunch that we enjoyed.
When researching our trip to the Berkshires, the Hancock Shaker Village came up multiple times as a must stop. I will be honest, this did not interest me at first but I marked it down for our final day of the trip in the event we had a new found interest and time to do so. And I have to say, we had a really great visit here and I am glad we ended up doing so!
Read about our visit to the Hancock Shaker Village here!
On our way back home, we stopped at Hilltop Orchards and wow this place was bopping. We had to park down the hill in order to find a parking spot! Though we were just here for the apple cider donuts – which were being freshly made by the machine just outside the barn – Hilltop offers a variety of baked goods. But what attracted the crowd is the cider and wine bar and while we did not have time to try some, the amount of people here certainly is testimony to it. The cider donuts here were extra crispy on the outside from the frying process and had a slightly spiced flavor.
And that is a wrap for our long weekend exploring the Berskhires. There is so much going on in this area of western Massachusetts and it really makes for a wonderful fall foliage travel destination.
Read all blog posts for the Berkshires here!
See our complete itinerary here!
Planning your trip? Check out the Perfect Fall Itinerary to the Berkshires here!
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