Day trips to The Berkshires and Litchfield Hills

Friday I set out on a solo day trip to the Berkshires – the county in Western Massachusetts that is known for its beautiful mountains. My first stop was Mount Greylock, which is the highest peak in Massachusetts. It was a stunning drive up the mountain, which is 3,498 feet above sea level. At the top I was very surprised by how cold it was. It was a very chilly and windy 46 degrees and I was freezing in my fleece North Face jacket. I had to wear my hood because it was that cold! The top offered a breathtaking view of a town below (I’m not sure which one). At the top there was a lodge with a café and even a few guest rooms. I was very surprised by the amount of people over 50 I saw hiking on the mountain. Good for them!

Next I went to Williamstown, which is up in the Northwest corner and just miles from New York and Vermont. It is home to the liberal arts school Williams College. I stopped for a little at Tunnel City Coffee, which was fairly busy. It had a great selection of sweets and an average sized selection of coffee drinks. The downtown area that the coffee shop is located on is called Spring Street and is about 3 blocks long. It did not have many restaurants and stores, but it did have a North Face store.

I then stopped at Berkshire Outfitters in Adams to rent a bike. The shop is located only 300 yards from the Berkshire Bike Path, which is a beautiful, flat path. I joined the path about 2.5 miles in and biked to the other end, which was roughly 8.5 miles. It took me 45 minutes to reach the end at a somewhat fast speed. At the recommendation of the guy who rented me the bike, I stopped at a place just off the trail called Whitney’s Farm. I got some hot apple cider and a pumpkin doughnut.

On my way back to Westfield I took a road called Mohawk Trail (Rt. 2) that goes east-to-west in a part of Massachusetts called Pioneer Valley. I read somewhere that this is supposed to be the best fall foliage drive in Massachusetts, but I didn’t think it was anything special. Also, part of the trail was closed, which I knew about in advance, due to water damage.

On Sunday I explored Northwestern Connecticut, known as the Litchfield Hills with my roommate Kelly and Brittany. This is the part of Connecticut that inspired the town in the TV series Gilmore Girls, which I am a huge fan.

Our first stop was Litchfield, which had a tiny downtown with upscale stores and just a few restaurants. Next we drove through Washington Depot, the actual town the creator of Gilmore Girls said was the inspiration for Stars Hollow. From my research beforehand I knew there wasn’t anything special about it, so I don’t really know how this town was the inspiration for such a vibrant fictional town!

 

The Elephant’s Trunk Bazaar in New Milford is a huge flea market that takes place every Sunday from April through November. There were rows and rows of random items and antiques. Downtown New Milford consists of a block of shops, a movie theater, and Bank Street Coffee House and a few other streets with restaurants. At the coffee shop I got a pumpkin pie chai and Brittany got chaider (chai and apple cider). We both LOVED our drinks. Something that I had never seen before and seemed really “small town” was the “Buy Your Friend A Drink” board. I didn’t really get the small town feel the short time I was walking around the downtown, except for the restaurants I passed, which did look like places locals eat.

We were all getting hungry, so for lunch we stopped at Villager Restaurant in Kent. I read online that this place is very popular with the locals. When we walked in we were waiting by what looked like a host’s stand, but when one of the waitresses passed us and said “there’s an open table over there,” I realized this is one of those places you seat yourself. The food came fast and was good. We walked down Main St. though the main part of downtown, which was about 2 blocks and had a few restaurants and shops, to Belgique Chocolatier. Here I had the most rich and delicious hot chocolate I have ever had. And the whipped cream on top was the best I’ve ever had. This was our most favorite town because there were several people out and about and it had beautiful views from the downtown.

Next we visited The Sharon Audubon Center Trials. This had a lovely garden, pond, trails, and even an aviary! There were several birds that were rescued because of injuries and wouldn’t be able to survive in the wild. We saw a bald eagle up close, which was incredible.

On our way back we drove through Salisbury and Norfolk, which were supposed to have cute town squares, but there was anything special about them. Close to the Massachusetts-Connecticut boarder there was an amazing scenic stop. I had never read anything about this and it is truly a gem and a must-see for anyone in the area. It is located on Saville Dam Rd. near Barkhamsted.