Five Hikes in the Berkshires!

Hey all! Happy FRI-YAY! Or as I like to call it “Happy Josh has a day off tomorrow!” Because what’s happier than your husband being home and helping out? Nothing? I AGREE.

This week was vacation week and man was it FUN! I wanted to share with you our five hikes we did each week day this week…that’s right five! Guess we’re getting ourselves in shape for the summer time. I’m just throwing this post together as a quick look at some adorable photos and also some reference for anyone visiting the Berkshires or North Adams. All these trails were less than 45 minutes from Main Street in North Adams! I’m going to let you know how each one was for the kids as well as how I felt about them.

Brook and Berry Trail, Mount Greylock

This was a hard trail! We followed it in about a mile and then turned around because I wasn’t sure how long it was or where it came out. There were quite a few uphill areas I was worried about going up with Bear on my back. The trail itself was well kept and okay views. The brook was pretty but no berries yet. However If you’re looking for some stunning photos, I’m not sure I would recommend the first mile of this trail. Again, I only went a mile in and turned.

The kids DID love it because there was a lot of things to pick up and they really enjoy the brook. The hike we did took about an hour and a half. Again, it’s pretty hard! If you’re not an experienced hiker or going with little kids, I caution you on this trail. We probably won’t be taking it again with the kids.

Bradley Farm Trail, Mount Greylock

If you’re a newcomer to the area who wants to drive up to the top of Mount Greylock then take an easier stroll through the woods? This hike is totally for you! With the entrance right next to the visitors center and a fun 2.3 mile hike, it’s great for kids. There’s still not as many great views to look out on with this hike.

I really say this hike is great for kids. There are a few places where I was just a little worried because the side of the trail was a little bit of a steep fall. It was mild though!

Rail Trail (Cheshire Entrance)

We entered in through the Cheshire entrance for our Rail Trail hike. I chose to use the kid bikes and packed a lunch. We walked about a mile in, had our lunch by the lake, and walked back out. This walk was so easy! The path is paved for bikes. The road is flat. The only part that caused any worry is crossing the high way. But they made it so easy by adding a stop light!

The sights on this hike were nothing short of stunning. Looking out at the lake was such a blessing. It was a little chilly right there on the water, so if you’re with kids, bring a sweatshirt!

Shoreline Trail to Lookout Point, Clarksburg

The kids LOVED this hike. I have a special connection with Clarksburg State Park. We frequent it during the summer months.


We chose to walk the Shoreline Trail to the Lookout Point then turn back around. Once we hit the parking area, we went down to the Blueberry trail and walked the beach. Then we followed the road back up to my car. All together this was a little over two miles. It’s a fairly easy hike to make and the sights you see are spectacular. I cannot recommend this hike enough. The staff even recently fixed the bridges on that trail and they were amazing.

Be forewarned though-this is a SHORELINE trail! It’s wet all year round but you sink a few inches during this wet season.

Natural Bridge

On our final weekday of vacation, Princess and Monkey had slept over Mema’s. Doodle was still on her mission trip. Josh was at work. It was Bug(3), Bear(1), and I. We headed out towards Natural Bridge! I’ve written about Natural Bridge before and it’s a great hike, but I want to add in today-if you’re an art enthusiast, there’s an area with some great statues the boy LOVED to look at! This trail is super easy but has beautiful sights. And in the summer there are a few areas to wade in!


I hope anyone who just had April Vacation had a blast! I know we did.

2 thoughts on “Five Hikes in the Berkshires!

  1. Great pics! I’m thinking about taking my boy on a nature hike, which he’s never done. Now I know it’s possible with a little one, lol. Thanks for sharing!

  2. Lara says:

    Those views in the last couple are beautiful! It’s hard to find hikes that are good for kids, thanks for sharing!

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