Crawl In “Boston Winter”

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When we’re not organizing bar crawls, we still find ourselves visiting bars and fun spots around the city.

Boston Winter


The adventure began at Boston Winter located at City Hall Plaza. We found Vinopolis and enjoyed a flight of red wines while enjoying some live music.  Boston Winter, in its second year, is an extremely welcome addition to the usual eyesore that is Government Center Plaza.  With ice skating and local shops selling gifts, this Christmas market has a European feel that is unique and fun.

After an icy walk through City Hall Plaza, we remembered that a wine shop was now open in the Boston Public Market. And it didn’t take us long to find the Massachusetts Farm Winery and Growers. They were offering a $10 wine tasting which seemed perfect. I honestly thought we’d try 4 or 5 different samples. Maybe our server was bored or maybe it was par for the course, but I think we had 12 each. I lost count as they kept coming, supplied by our cheerful and chatty host. Best $10 investment ever, including souvenir wine glasses.

Next up was The Hard Rock Café. We had enough wine for the night and they have some excellent coffee drinks to warm you up on a cold night. We met a nice older couple from Quincy who comes here every week. They were favorites of everyone at the bar it seemed, and we liked them quickly as well.  She’s a fan of the Red Sox and the rodeo, he’s big into Broadway, and they were lot of laughs.


Up next was a quick walk over to Christopher Columbus Park to check out some holiday lights.

We continued to Faneuil Hall to see the 85 foot Christmas Tree.

We quickly realized it had been a very long time since we had last eaten. And one of our favorite burgers was within walking distance. So we headed over to JM Curley which also happened to be Star Wars night. Besides burgers, this is a great spot for cocktails, beers and snacks (try the bacon popcorn!) Hidden in the back is Bogie’s, an amazing, tiny steakhouse that serves superb steaks in a cool setting.

We finished it off at No. 9 Park. The famous Tom and Jerry is only available annually from first snowfall until Valentine’s Day. It’s like a warm egg nog and a hug. One of Boston’s nicest restaurants, No. 9 Park overlooks the Common and when the Christmas lights are on, it’s one of the most romantic spots in town. They also have an extensive classic cocktail menu, and they make a mean martini.




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