Our First Trip to the Berkshires (Weekend Guide)

Happy Monday friends! I'm just going to jump right into today's post because it's going to be a long one. As you know, last weekend we made our first trip to the Berkshires and we absolutely LOVED it! Obviously we are total New England newbies but I still wanted to share if y'all ever plan a trip because if we go back we pretty much want to hit all the same spots all over again!

 Where we Stayed
The Berkshires covers quite a few cities in Western Massachusetts from what I can tell. We stayed North of Mount Greylock between North Adams and Willamstown. Both towns were SO adorable and I'm pretty sure when we will go back we will stay in the same area.
North Adams--the dowtown area of where we stayed
I am SO sad I can't remember the name of this little spot but we pulled over to take pictures because it's right on the edge of  a mountain--gorgeous views and I think it's a restaurant too!
We didn't have many options for lodging because we booked sort of late and also we had the dog. Any of y'all that travel with your fur babies frequently probably know the struggle of finding a nice pet-friendly place! We just stayed in a little motel that was clean enough but the room was SO small and outdated so for that reason we probably won't be going back. The main thing I liked was it was SO close to a lot of different restaurants and it was so easy to get to Mount Greylock where we ended up hiking. There also was a gorgeous park that was only a couple minute walk away so it was perfect for letting Toby off leash to explore. A local couple we met there told us it used to be a trailer park years ago that got destroyed in a hurricane.

We ended up getting drinks at a new resort down the road from our motel and discovered that they actually take dogs so we will definitely be staying there next time! It's called Toursists in North Adams. They had a gorgeous outdoor bar with fire pits and the prettiest view of the foliage. If you're planning to make a trip I would definitely recommend checking them out even though we haven't stayed there yet!

Drinks at the patio bar at Tourists

Where We Ate
We honestly grabbed a lot of stuff on the go since it was such a quick trip but we did have a nice sit-down meal at two places that were just AWESOME. The food was amazing and we also found a really cute little coffee spot!

We were staying VERY close to Williams College which is surrounded by this gorgeous little downtown area. We grabbed coffee at the local spot, Tunnel City Coffee. I got a Chai latte and Steven got an Americano and we loved them both! Highly recommend stopping here then exploring the campus because the foliage was SO dreamy!
This spot had to be our favorite from the weekend! The restaurant is called Trail House Kitchen and Bar in North Adams and it seriously was the cutest little spot. SO cozy and Steven and I were REALLY impressed with the food. I got the stuffed shrimp and it was amazing! 
For dinner one night we went to a newer restaurant called Public which was in the downtown part of North Adams. They had an awesome drink selection and it seemed like a very happening spot! The food was also super yummy. 

What We Did

Our first day there we mainly explored the area. We walked around downtown North Adams then we ended up taking a drive through part of Mount Greylock. We wanted to just scope out the different hiking spots because that was what we planned to do most of the day Sunday.

Aside from North Adams, we also LOVED walking around Williamstown and the Williams College campus. I took SO many pictures of the foliage there but here is one of my favorites:
On Sunday, we spent most of the day hiking Mount Greylock. We picked a trail that was relatively easy and good if you have your dog with you. It probably only took close to 2 hours and the foliage was just gorgeous! 

After hiking, we decided to drive further up the mountain to get some good views. Unfortunately it was pretty foggy so we didn't see a lot the further up we went! 

Sunday night after grabbing an early dinner at Public we were pretty exhausted so we ended up just grabbing desserts from the local market near our motel and of course had to snap a picture of Toby with some pumpkins!

Now that is a great picture for the finale! Hope y'all enjoyed this little recap!
[Linking up with Biana from B Loved Boston]


  1. We were so close to the Berkshires this weekend and it's seriously just stunning there! I love all your fall outfits and can't wait to go next year! xo, Biana -BlovedBoston

  2. What a wonderful trip and fall get away!! You looked adorable, always do!!! Love it all!

  3. I love your pictures.
    It looks like such an amazing place !

  4. I can't get over how beautiful all of these photos are!! Such gorgeous trees and backgrounds!

  5. Those photos are stunning! So much fall goodness!

  6. I am so jealous of all of your fall fun! The leaves changing are so pretty! Such a perfect little getaway. And I have to ask... what filter are you using?! I am OBSESSED!

  7. This is such a cozy and chic look dear, loving your sweater, especially the orange one! Cute photos too!

    Jessica |

  8. This just looks SO up our alley. I'm glad you guys had such a wonderful time!

    Katherine |