Tales Between Trails: Massachusetts to Maryland Part 1

Saturday, September 28th, 2019

The challenge begins! The goal? Make in back home to Maryland from where we currently were in Williamstown, Massachusetts. The mode? Hitchhiking.

We started our journey by strolling down the road. Williamstown was a cute little New England town and we wanted to explore a little bit. We were in no rush.

We asked a local liquor store if we could take some cardboard off their hands and borrow some markers. I created a short, simple sign to help us with our mission which said one flexible word: “SOUTH”.

When It was time to get moving, we went to the proper intersection, stuck out our thumbs and began to dance. A New York couple named Travis and Billy were heading to Vermont to do some leaf peeping. We shared some stories while they drove us 20 miles down the road to Pittsfield, MA, which was as far as they could take us.

We wandered around Pittsfield and looked in some shops after eating at Burger King. We tried to hitch, but no one was biting. We shifted down the road a couple times and tried different intersections. No luck. There was a Ben and Jerry’s across the street, so we told ourselves, if no one helps us out after 3 more traffic light changes, we were getting some ice cream. We ended up getting ice cream.

When we tried hitching again, we got lucky. A golfer named Jeff wasn’t going far, but he told us we seemed safe enough to pick up and took us another 13 miles down the road to a little fire station in Stockbridge, MA.

It wasn’t 2 seconds after getting out of Jeff’s car that another guy picked us up to take us 10 miles down the road to Great Barrington, MA, an Appalachian Trail hiker town that we knew we could hitch further out of. His name was Tim, he lived in Great Barrington and thought we seemed safe enough, but he made an Instagram story starring yours truly just in case. He dropped us off by the grocery store which was next to a pot dispensary with a massive line out the door. They would have some entertainment as they waited. We danced by the same intersection until a girl named Greta pulled over.

She told us she was picking us up to hear some good stories, unknown to us at the time, she was the one with all the stories! She told us about being in real estate, flipping bungalows while also being a scuba instructor on Honduras’ Roatan Island. The creole locals apparently all had the surname “Morgan” and were the descendants of pirates. She told us about hiking the Camino de Santiago in Europe, spending time in an Ashram with Hare Krishnas, teaching in Spain, and riding a motorcycle with her former boyfriend all the way to Peru. Not only were we enthralled by all of her incredible stories, she drove us all the way to New Milford, Connecticut!

Our next hitch was short, but like all of the ones before, absolutely appreciated. The driver’s name was Cody and he was a firefighter with his cute pup, Genn in the passenger seat. He dropped us off up the street in Dandury, CT.


To be continued …

2 thoughts on “Tales Between Trails: Massachusetts to Maryland Part 1

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s