After returning from my trip to Rhinebeck, I am struck with how thankful I am that I was able to attend and all of the beauty I experienced. In addition to the NY Sheep and Wool Festival, I was also able to tour around the New England area – a trip I’ve wanted to take for probably a decade. What made it even better was that I was able to time this trip at a time when the trees were absolutely stunning. Nearly the whole drive consisted of a hallway of red, orange and yellow trees. I did choose to drive rather than fly for a few reasons. First and foremost, flying gives me a lot of anxiety. Secondly, you can have so much more flexibility when driving – from where you can go to how much you can bring with you… or buy and take home with you.

Part 1: Portland, Maine

After two and a half days of driving, we arrived at Portland, Maine. This was the only place we needed to use our winter coats. We drove into town and had dinner at $3 Deweys.

The next day we drove to Portland Head Light to see the lighthouse that is there. We were also able to tour the museum that was also located there. It was very informative and interesting to hear about the history of the lighthouse, including how it developed over the years, being built taller or shorter based on what was believed to be the best height for ships to be able to see at the time. There is a list there of every Lieutenant who was responsible for it over the years. I also found it interesting that there was a period of time where they did not light the lighthouse so that it would not lead enemies to a safe arrival.

We did a little shopping the rest of the day and enjoyed our time there.

Part 2: Boston

The next day, we drove to Wakefield, Massachusetts and took a train into Boston. I have been told by multiple people NOT to drive in Boston, and I am glad we didn’t! It was just around a 40-minute train, and then we were off and running. We walked to Sorelle Bakery and Cafe for coffee and a pastry before continuing on to see the USS Constitution and USS Cassin Young – two impressive boats that we were able to tour.

From there we walked to Newbury Comics in Faneuil Hall Marketplace. I came away with a Stardew Valley cookbook, which I am very excited to try some recipes from.

We continued on to the Boston Commons, Cheers and then took a train to Cornwalls for dinner. It was then 5:00 pm, and we chose to brave the train at rush hour to get back to our hotel for the evening. Thankfully we got a train that was not very busy and had an enjoyable ride back to our car.

Part 3: Indie Untangled

The following day, the only goal was for us to make it to Indie Untangled by 4:00 for our shopping time slot. It was going to be around a 3-4 hour drive, so we leisurely got up and had brunch at a delicious local spot called Half & Half in nearby Reading, MA. From there we drove to the Indie Untangled event and arrived around 3:30.

There were 3 separate tents full of vendors selling their hand-dyed yarns and other goods. There were so many options it was hard to choose what to buy. In the end I purchased a dark green tonal fingering yarn for my Market Henley sweater I’d like to make by Perfectly Knotted. Additionally, I couldn’t leave behind the below set of autumn tonals.

And what a gorgeous location to shop!

That evening, we had a delicious dinner at a local favorite in Marlboro, NY, called the Raccoon Saloon. According to our AirBnB hosts, it’s where the locals go, has a great view of a waterfall, and is haunted. Obviously, we had to go. We were surprised to find the owner is Irish, and he and my British husband had a lovely chat like old friends. The food was also delicious – clearly the locals have great taste.

Part 4: NY Sheep & Wool

The morning of Saturday, October 19, I put on my Framed Sweater, ready for the festival. It was a gorgeous day to be outside. We had about an hour drive to arrive at the Rhinebeck fairgrounds, and we enjoyed every minute of it.

Once we arrived, it was quite daunting seeing the sea of cars that had already parked. Walking in, however, there was still plenty of room to walk around and see all of the beautiful yarn, bags, sheep, and more.

At around lunch time, we walked down toward the food vendors, which is when I took the photo of the huge group of people below. At this time we decided enough money had been spent, and we were ready to go out and get some lunch in town, rather than wait in a long line for a vendor at the festival.

After lunch, we hiked to a fire tower. The photos from that are in the following section.

Below are the items that I purchased:

Last Thoughts

What a beautiful place to be! I have been on a lot of roadtrips before to different places, and this was definitely one of the most beautiful ones. We had beautiful views from our drive, to the view from our AirBnB in Marlboro, NY, and the hike to a fire tower in Rhinebeck, NY to the view from the top (which I did not walk up to, but my husband did to get that beautiful photo).

One surprising thing to me was the sheer amount of Dunkin Donuts there were. At one, we were given an extra chocolate donut, which was a nice surprise. I’ve learned that I cannot order a mocha at Dunkins, but I CAN order a latte with mocha flavoring.

Even though it was a very long drive, I would recommend it. I may not be able to attend another NY Sheep and Wool festival, but the memories made on this trip will last a lifetime.