Road to the Altar: A Romantic Weekend in Boston | Outtraveler

Road to the Altar: A Romantic Weekend in Boston

Kit Williamson

On Valentine’s Day, John and I decided to take a day trip from New York to Boston. It was the coldest February 14th on record for the city, with temperatures hitting minus 9 and a windchill of minus 36, but we weren’t going to be deterred—we were on a mission to have the most romantic day possible, since we were going to the birthplace of the American Revolution to pick out our wedding rings. It was also a nice break from the frantic planning leading up to our wedding at the end of the month; less than two weeks to go and panic was starting to set in. We’d tried to keep our wedding small and easy but were quickly finding there’s no such thing as a small and easy destination wedding in Palm Springs.

It’s very convenient to get to Boston from NYC by plane, high-speed train or bus. We chose to take the bus because, like I mentioned, we were planning a wedding, and didn’t want to fall into financial ruin. It was a little over four hours on the Megabus, which felt a lot quicker because there were outlets and wifi on board. After we agonized over which picture to Instagram for an embarrassing amount of time, we wrote the ceremony for our officiant and finalized a few last minute wedding details.

Kit Williamson

Images via Instagram.

We had chosen a sustainable jewelry company that we found online, Brilliant Earth, that happened to have a showroom in Boston, and we didn’t consider how fitting it was for us to travel to Massachusetts for our rings until we were on our way. In 2003, Massachusetts was the first state to legalize gay marriage, sparking another revolution in America, this time for marriage equality. Prior to that, in the 1970s, Boston was the birthplace of The Gay Community News, the legal advocacy group Gay & Lesbian Advocates & Defenders and the home to the country’s first openly gay state representative Elaine Noble. In his book Out of the Past: Gay and Lesbian History from 1869 to Present, Tufts University professor Neil Miller makes the argument that Boston “represents a missing piece crucial to understanding the formation and growth of gay institutions…nationwide” and like we observed in New Orleans, you can feel the city’s history on every block.

Boston has a thriving LGBT community, with the largest population in the South End and Jamaica Plains. Although we weren’t staying in the gayborhood, we felt comfortable holding hands and being affectionate everywhere we went. In the future, I’d like to go back to explore the nightlife more, but for this trip we were on a mission.

Upon arrival, we checked into the Nine Zero Hotel in the financial district because it was convenient to both the Brilliant Earth showroom and Boston Commons. After a quick glass of free red wine in the lobby (remember, we’re on a budget here) we took an Uber to the showroom to try on our rings. We ended up both liking the Mojave Matte rings, which sounded fitting for our desert wedding in Joshua Tree, and we enjoyed learning more about Brilliant Earth’s mission of sustainability and fair labor practices; they donate a portion of every sale to a region that has been aversely impacted by the industry.

From there it was a short walk to the Boston Park Plaza Hotel, where we both ordered an Over the Charles, a reference to the Charles River and their take on a dirty martini, with vodka, vermouth mist, olive brine and blue cheese stuffed olives. Although it was freezing, we decided to walk through the Common to our dinner reservation at Teatro, a trendy Italian restaurant with homemade pasta and blue lights shining up at the ceiling. The Commons is reminiscent of the more heavily trafficked parts of Central Park, with dozens of lampposts lining every path, shining white light on the thin layer of snow on the lawn. It’s inspiring to think of all the protests and rallies that have taken place here throughout the years.

The church spires and historical buildings on seemingly every street corner don’t feel anachronistic in Boston, rather, the modern buildings are the ones that feel out of place, granting every brick and cobblestone lined street a feeling of gravitas and significance.

Kit Williamson

Images via Instagram.

The next morning, we decided to walk The Freedom Trail, a 2.5 mile long, self-guided tour of Boston’s historical sites, which begins at the Commons and includes Paul Revere’s house and the site of the Boston Massacre. It was a little warmer, and we felt we’d regret leaving Boston without seeing at least one person dressed up as a founding father. The trail led us, naturally, to a mall and food court called Faneuil Hall, complete with a bar decorated like the set of Cheers, including cardboard cutouts of Rhea Perlman and Shelley Long. Apparently it is often referred to as the “cradle of liberty” because of its role as a meeting place and market during the revolution. There was also a ice throne with roses frozen inside of it, which we took a very romantic picture on. No one heckled us, which was a nice confirmation of the feeling of welcome that we had experienced since arriving.

Everywhere you turn, Boston strikes a nice balance of silly tourism and inspiring history, and I’m definitely looking forward to future trips to the city, maybe on our way to explore Provincetown, which I’m overdue to see. To close out our time in Boston, John grabbed a Lobster Roll at the food court and we hit the road back to NY, one destination closer to the altar. 

Kit Williamson

Images via Instagram.

KIT WILLIAMSON is an actor, filmmaker, and activist living in New York City. He best known for playing the role of Ed Gifford on Mad Men and creating the LGBT series EastSiders, which is available on Vimeo On Demand

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