• thewanderingprofessional

Why You Should Visit the Lower Berkshires this Fall

Updated: Nov 6, 2020


Every year I try to pick one day in October to dedicate to all things Fall. I am talking some type of combination of apple picking, pumpkin picking, corn maze, fairs, etc. Unfortunately 2020 left this years Fall Day coming up a bit short for obvious reasons (I do not know what I am going to do if everything is canceled next year again [insert sad emoji]). But alas I tried to stretch out as much normal fall things as possible this year. And to put a spin on it this year, decided to get out of Connecticut for this years Fall Day (since I have left the state once since February).


I decided it was time to take a trip up to the Berkshires, a place I had only been once before for a white water rafting trip in College. And this is why you should take a trip up to the Berkshires this year as well.


Early Morning Hike

Is it really a true fall day if there is not any hiking involved? I mean, one of the main draws in New England in the Fall is those beautiful changing foliage colors. And since the Berkshires has a lot of rolling green mountains like Vermont you bet you will find a ton of hiking and ways to see that beautiful New England fall foliage.

Beartown State Forest is a perfect place to go hiking in the lower Berkshires due to its size and being pretty smack dab in the middle of the Berkshires. The Appalachian Trail also cuts right through the middle of the Forest. The Forest allows for a lot of activities beyond hiking such as snowmobiling, hiking, skiing, and snowshoeing. It should also be noted that after Labor Day there is no parking fee otherwise it usually costs $30. We took the Benedict Pond Loop with an offshoot to the Ledges. The hike was fairly easy with only a 200 ft vertical climb over a half mile to get to the ledges but beyond that it was fairly flat. The view was great looking right over those rolling mountains to the West once you hit 'The Ledges'. There is also very little service here so I would recommend knowing how to get out of Beartown and saving a picture of the trail map to your phone. We also got here early, since I believe the best way to beat crowds is to go early, but when we arrived we were one of only two cars there and upon leaving we were the only ones in the parking lot. So it seems AllTrails was right on this being a lightly trafficked hike.


But Second Coffee

Once done hiking, I recommend taking a ride up to Stockbridge. This quaint town just off the Mass Pike has all the charming New England town vibes one needs. It has that local B&B right in the heart of downtown and every store front is a locally owned business with not a chain in site. The sidewalks are covered in brick and stone and lined with large colorful trees that could be the backdrop for any fall movie. The town is not very large so can easily be walked around in an hour. This is also the perfect town to grab that second cup of coffee (since I know you already had your first when you woke up extra early to be the first on the trails). You can grab a full classic breakfast from the Main Street Cafe or keep it simple and grab some coffee from Stockbridge Coffee & Tea. We settled on grabbing a delicious croissant and coffee and hot chocolate from The Lost Lamb and enjoyed it on the sidewalk patio in front of their shop. This town also seems like a great place to grab lunch as well, the dinner options seemed to be a bit more slim picking here though.


Make sure to stop into all the little shops that call this place home. The chocolates at Peace, Love & Chocolate almost looked too good to eat. There are also several gift shops to check out like Sidetracks, or pop into a vintage market or art shop. You will feel like you just took a trip to Stars Hollow when you are done here.


Museums + Gardens

The surrounding Stockbridge area is full of Museums and Gardens to check out. You can pay a visit to the Normal Rockwell Museum, visit the historic Chesterwood, visit famous writer Edith Wharton's The Mount home or stroll the grounds of Tanglewood. But to get in the fall spirit there are two options. Pay a visit to the Berkshire Botanical Garden for their annual Harvest Festival. Each weekend they have a different theme from kids weekend to bands and brews. They have food trucks and local breweries every weekend and can enjoy them spread out on their property. You can stroll the property and wander through the gardens and trails. Or pay a visit to Naumkeag and walk through their property full of carved pumpkins to get in the Halloween spirit and mums to give you all the fall feels.


Apple Picking Time

Can you really say you did all the fall activities if you did not visit a single apple orchard? There are a couple orchards you can stop at in the lower Berkshires. One is the Hilltop Orchards in Richmond. This orchard is huge with tons of apple varieties, although it was a bit of a mess trying to figure out what each apple was and lots of people just doing their own things in the orchard like having picnics and photo shoots. So this was a bit distracting while trying to enjoy the fun of finding the perfect apples but still enjoyed our time there. But this orchard is nice because it has its own winery on property to get bottles and samples to enjoy before or after your apple picking. And the apple cider donuts were soooooo good! Another orchard you can check out is the Windy Hill Farm in Great Barrington. This one also has a large selection as well and nice views if you trek to the top of the orchard. There is also another great hiking spot right next to the farm if you want to hike up Monument Mountain instead of Beartown.


Just down the road from Windy Hill Farm is Taft Farm which has a small farmers market that makes delicious deli sandwiches. They also make a lot of homemade products to check out as well. Although no apple orchard here, they do have a corn maze you can work your way through. We skipped due to our timing and how long corn mazes usually take us.


Finish Your Day in Great Barrington

Great Barrington reminded me a lot of where I currently live in West Hartford and I think that is why I enjoyed it here. It has a very small city vibe but still local and charming. There is a bunch of restaurants, stores, galleries and bars scattered throughout the downtown core. It is also right on the Housatonic River with a small river path you can explore. Rubiners Cheesemongers had all the charcuterie needs, Sett with the cool kitchen and tableware and Soco Creamery for those sweet ice cream vibes. If your here in the morning check out Fuel or Marjoram+Roux for your breakfast and coffee needs. If your here for dinner two places came up as recommended, GB Eats for a modern diner flair and Baba Louies for their sourdough pizza. We opted to go a little out of downtown on our way home to The Bistro Box, only to find out they're closed from 3:30-5, so beware of their hours before coming. Their menu is simple but the food looked good. They also have a large yard to eat out in and play games. Also down by The Bistro Box, if in the area in the morning/lunch time, is Great Barrington Bagel Company which also came recommended, we were too late in the day to check it out unfortunately.


The town also has one of the only breweries in this area of the Berkshires (how is a good question with the booming craft breweries in this country), Barrington Brewery. There are also a few other restaurants you can check out in the brewery area. The Housatonic Flats Reserve is also across the street but I would probably recommend skipping, it was a bit uneventful of a "hike". The Mielke Confections chocolate shop is over in this area as well if you did not get enough chocolate fix in Stockbridge.


If you have more time in the area also pay a visit to the towns of Lenox and Lee. Both towns are quintessential New England small towns with quaint downtown areas. Both are like Stockbridge and Great Barrington filled with local restaurants and shops to browse through and eat to your hearts content. If you need something a bit less small town, Lee is also home to a large outlet mall shopping area for all your shopping needs. You will definitely have plenty of options of things to do in this area.


Let me know if you take a trip up to the lower Berkshires this Fall. If you have any favorite places in this area, let us know! Enjoy wandering.


-The Wandering Professional



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