The Berkshires travel guide is here! It was our first time visiting the area this fall and we absolutely loved it! Tim and I took a little weekend getaway to Stockbridge, Massachusetts to celebrate our 3rd wedding anniversary and it was the most cozy, relaxing time. I also vlogged the trip for YouTube HERE, if you want to watch some highlights too.
We planned our trip around the beautiful, historic Red Lion Inn and knew we wanted to really soak in the fall season. It was the perfect location- right in town and walkable to all of the shops and restaurants! Stockbridge itself is also close to several other towns and attractions, so we were always less than 15 minutes from the next activity!
Berkshires Travel Guide
Friday:
Friday night we drove up to The Berkshires from NYC after work and it took about 2.5 hours. We arrived to the Red Lion Inn, dropped off our bags and went down to the Lion’s Den for a quick bite. They had fun live music going too! We explored the property a bit and went to bed to rest up for our day of exploring.
Saturday:
On Saturday morning we were so excited to shop around the cute Main Street! The sun was shining and the leaves were in peak foliage, so it was beautiful. We shopped around and grabbed a quick bite at Main Street Cafe before driving over to the Shrine of Divine Mercy. We explored the grounds there and then headed to the Norman Rockwell museum. It was actually super cool to see his work and all of the “Saturday Evening Post” covers.
While at the museum, we found a cute vintage lamp that said it came from Great Barrington Antiques, so of course we had to venture there next. It was amazing!! They had a ton of different vendors set up in the antique shop, and we really could have spent hours there. We grabbed a soup and sandwich lunch at a market nearby and then stopped at a few more shops on the way back to Stockbridge.
Next up, we had tickets to the Naumkeag Pumpkin Show– where they have a ton of carved pumpkins on display throughout the grounds and mansion. This was such a fun way to celebrate the season since Halloween was a few days later. We had dinner back at the hotel’s restaurant and loved how cozy it was! We listened to the live piano music and played some chess to end off this night.
Sunday:
For our last morning, we grabbed breakfast at the hotel and explored town a bit more. We headed to mass and also shopped at the two cute stores on the property. We headed out around noon, and were already chatting about coming back! The town looks like it’s adorable for Christmas too… so that’s definitely on the list again. 🙂 Overall, we loved visiting the Berkshires in the fall season and definitely recommend the Red Lion Inn, too!
Let me know if you have any questions! Want help planning your trip? Send me an email: Lauren.rueter@fora.travel
