A Weekend in Boston: Kayaking on the Charles River, Paint Nite and Michael Che Comedy Show

A Weekend in Boston: Kayaking on the Charles River, Paint Nite and Michael Che Comedy Show

Last weekend, I drove to Boston to visit my college friend, Jenny. We live five hours from each other, so we don’t get to see each other as much as we would like. Every time we do, we try to make the most of it.


We had dinner after I arrived and then we headed to Common Ground Bar and Grill in Allston to have a drink. It was a cute place with a nice selection of beers and ciders. We then caught an Uber to The Wilbur for a comedy show. I had only been there once before to see Thunder Down Under (who were absolutely amazing! Check out their tour here).

The show was headlined by Michael Che, who is most known for Weekend Update on Saturday Night Live. The comedian who opened for him was hysterical–all of her material related to the struggles of having kids and the journey of her marriage. I loved it because it was so real and raw. Even though I’m not a mother or married, I felt like I could really connect with her “struggles.”

After her performance, Michael Che’s “pump-up man” turned out to be a comedian himself, and he performed next before introducing Che to the stage. Che put on an entertaining performance as he interacted with people in the audience, poked fun at Trump and told a story about the last time he was in Boston in which a drunk man wouldn’t stop pulling the hood of his jacket over his head. He also named Boston as the most racist city in the country, which received many denials from the audience. You can read more at the Boston Globe. At the end of the show, he brought a few audience participants up on stage, including a man who looked like Santa (yes, I’m not kidding).


Saturday was a packed day. Our morning started off with breakfast before heading down to Paddle Boston’s Allston/Brighton’s location, where we got in kayaks and set off. It was cheaper to do a double kayak, but we thought it would be more fun to do a single (a decision I regretted once we got half an hour into it–my arms were killing me!).

Lauren Taylar kayaking on charles river

The 5-mile trip to Kendall Square took us about two hours, and we passed beautiful boat houses, buildings belonging to Boston University and MIT, and eventually came upon the Boston skyline, which was such an amazing sight. It rained most of the trip there, but let up towards the end.

We capped the afternoon off with lunch at Chipotle, which was the perfect food to refuel with after kayaking.

Later on, we went to Brandy Pete’s where Paint Nite was taking place. There was a group of about 30 of us and we painted a sunset over the water. The instructor was very fun and lively. At the beginning, we took an oath of positivity and had to recite the phrase, “I promise not to say ‘Mine sucks’” (yes, really). The instruction was roughly two hours long and very easy to follow. I had a blast and I would definitely do it again!

Paint Nite Boston

Paint NIte Boston

Next, we had dinner at Tavern in the Square. I had a margarita and a cobb salad, which were both too good to put into words. The garage doors of the restaurant were open and between the breeze coming through and the food, it was the perfect place to relax after a long day.

Lauren Taylar Boston

Salad in Boston

Author: Lauren Taylar

Lauren Taylar is a digital marketer and blogger. She is a graduate of the State University of New York at Oswego, where she earned her bachelor’s degree in public relations. When she’s not volunteering her time with Make-A-Wish, you can find her reading a travel magazine and sipping a glass of hard cider or wine.


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