Activity Guide: 48 hours in The Berkshires

This past weekend I had the opportunity to take the most relaxing and scenic-filled a little over 2-day trip to The Berkshires! Believe it or not, this was my very first time visiting.  I can’t believe it because it’s such a short drive from the city and easy weekend get-away. Living in the city, I feel so blessed that I have the opportunity to experience all seasons and escaping to the blissful and breath-taking views and smells of nature. 

Last weekend while visiting, the weather was definitely on the chillier side. Most of the time that we were there, the air was cold and crisp; but there were still so many activities to enjoy regardless! That’s the beauty of the Berkshires. The Berkshires is definitely a top destination in the winter for skiing and in the summer to enjoy it’s plentiful lakes, picturesque green-grassy views while hiking and more. I wanted to take a trip in the fall to experience everything during the ‘off season’ and put together a fun travel guide of things to do during this quieter time in the Berkshires. 
Ben and I had a quick 2 1/2 days to experience all that we could, and we definitely did not have any downtime! I spent a lot of time researching favorites amongst the locals and tourists alike while in the area to make sure we didn’t miss a beat. I also had some fabulous recommendations from the team at 1Berkshire on some favorite places to visit. They were wonderful in orchestrating a busy schedule for us to ensure that we spent our time without missing a thing. We left on Friday morning and took a quick stop at the Lee Premium Outlets which are only about a quick 10-minute drive to the heart of the Berkshires. After the outlets we headed to our new home for the weekend, The Rookwood Inn  (more to come in another post about this enchanting victorian styled bed and breakfast in Lenox, MA.)! We took a quick little walk around Kennedy Park which before visiting I read so many positive reviews about this being a favorite and must visit while in the area. Kennedy park is filled with bikers, hikers, skiers and more. There are literally acres on acres of beautiful landscape and hiking trails to discover while here. The park was filled with the scent of fresh fall air and covered with crisp autumn leaves while drenched in beautiful sunlight! About 10 minutes into our walk we discovered a scenic little overlook with some benches and a crystal clear view of the mountains. I can definitely see why this is a favorite spot offering so many activities.
For dinner, we went to  a local hotspot, The Firefly Gastropub . 
This spot did not fall short of delicious comfort food, relaxing and inviting vibes and live entertainment while you eat. We had the most delicious food. while being surrounded by a warm fireplace and friendly local vibes. 
My favorite site was visiting MASS MoCA, (Massachusettes Museum of Contemporary Art).  MASS MoCA is located in a converted factory building and is one of the largest centers for contemporary visual art and performing arts in the United States. Around every single corner you could find another fun and exciting area that was rich with historical history. I loved the interlocking courtyards, each of them were filled with the colorful charm of all things Fall. Plenty of leaves and colorful trees everywhere you turned! I loved the gorgeous industrial touches the building offered, it completely added to the feel of the artistic setting. 

My favorite exhibit was the ‘Cosmic Latte’. By Spencher Finch. This exhibit was featured over 150 specially fabricated LED fixtures suspended from the ceiling over an expanse of the 80-foot long gallery. The lights are arrange in the shape of the Milky Way. ‘Latte’ refers to the overall color of the universe. This exhibit is available now through the New Year! You can always check their site to see what’s current at the time and what is upcoming.

Joe Wardwell’s Hello America: 40 Hits from the 50 States (Pictured Above)

Next stop: We visited The Berkshire Museum for the ‘Festival of Trees exhibit’ which is available at the museum from November 18th-January 7th, 2018. Christmas is my absolute favorite time of the year, so I was definitely in a winter wonderland and totally enjoying every second of this experience! The Festival of Trees offers a vast arrangement of fun, dreamlike and enchanting takes on dressing up Christmas trees. each tree had a unique object or ornament that became part of a fun treasure hunt for all to enjoy. Check out more photos below for some of the fun and interesting trees that we were able to come across! 
For lunch, we visited the cutest little cafe. We stumbled upon this while driving through the town and keeping our eyes peeled for something that looked and felt very ‘homey’ and somewhere where the locals would go for a fresh and peaceful dining experience. We found ‘On a Roll Cafe’ I tried their delicious version of a Fritatta, which was a delicious open-faced omelet and Ben had the New England Clam Chowder – when in New England right?!
Our next stop was to Greylock WORKS, Greylock WORKS is an insanely gorgeous modern space drenched with endless sunlight. We attend the Festive at Greylock WORKS which hosts everything from musical performers, local food craftors, local farmers, fermentors, distillers, and plenty of the regions best artisans. When not being used for the Festive, the space is generally used for a wide array of private events, such as weddings, fundraises and private forums. 
After a long day of new discoveries, we had another delicious dinner at Mission Bar & Tapas One thing I learned from our short time in the berkshires was that there are so many spots that are never fall short of a very warm and laid-back atmosphere. There’s usually entertainment at night starting around 8pm on weekends. Of course we were so tired, so we did not make it out that long! But we did have the most delicious meal! We wanted to order a couple of small plates at a time, but we ended up completely stuffed after splitting just 2 items! We tried the meatballs, which were in a delicious red wine sauce with shallots with caramelized onions and mushrooms. These are insanely delicious- I highly recommend! We also tried the mac and cheese which was so creamy and delicious- filled with different types of cheeses and breadcrumbs. 
On our final day, we were determined to pack a lot of things in, however, with the weather being breezy, cold and rainy, we had to cut a few of our plans of the day short. Our first stop was to hike Monument Mountain One of my absolute favorites views in the world is overlooking a high peak to a beautiful valley of trees and mountains. There’s just something so peaceful and tranquil about it that makes you forget about the rest of the world for a little bit. Unfortunately, we did not get the opportunity, but I’m excited to go back and make it one of my go-to stops! 
Our last stop of the day before heading home was to visit the legendary Norman Rockwell Museum The Museum is dedicated the education and art appreciation inspired by Norman Rockwell. This museum preserves and studies with a worldwide audience of the life and and spirit of Norman Rockwell. One of my favorite sightings was  to see the original Saturday Evening Post cover tear sheets features created between 1916 and 1963.

Norman Rockwell’s Studio Pictured Above

We had such a fun time and I’m so thankful that I was finally able to experience the beauty of the Berkshires! I can’t wait for another visit during the summer and the winter. Please visit 1Berkshire as a thorough guide of all things you need to know when planning your trip!

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  1. First of all your pictures are incredible and so many great recommendations. I will be heading to Berkshires in the spring and will have to visit all these cool spots. Book marking this post! Thanks for sharing! xo shalini

    1. I’m so glad that you liked it! You will definitely have such a good time in the spring when the weather warms up, so much to see and do! Glad this could be of help xoxo!

  2. This guide have so many great recommendations, I really need to visit, such a great place to unplug and wnjoy some down quality time!

    1. I’m so happy you liked it! Yes, it’s such a wonderful place to rewind and take some much needed “me” time! xoxo

  3. My oh, my! What a beautiful place you have taken us to! I can see how perfect it is for a visit anytime of the year. I love that it seems so peaceful yet has so many wonderful things to do while you’re there. I want to go!

  4. This sounds like such a fantastic place to vacation! I’m thinking of going with my husband for our anniversary ❤️

    1. It’s such a great anniversary spot! Especially the BNB I stayed in which I’ll be posting about this week! xoxo 🙂

  5. Wow this is an incredible guide! I have been wanting to make the cross country trip there (especially after seeing RHONYC, haha)!! But this post is perfect for knowing what to do, it’s on our list to visit next year!

    1. Haha yes! Same here 🙂 The good old Berkshires drama on the RHONY LOL. It’s such a dreamy location and so peaceful! You totally need to check it out! xoxo