RoamingRushka

April 2026 – June 2026

Journey to Boston

With a heavy heart, I said goodbye to my rock climbing friends at the crag at Pony Pasture in Richmond. The trek to Boston is a bit too far to make in one weekend, so thankfully, my parents decided to take a flight out east and spend a week at an Air BnB halfway to Boston to spend time with us and allow us to have a place to work for the week in between legs of the journey. 

We started the week in National Harbor, MD, which is an interesting little town that seems like it was designed for corporate getaways. It has all the Illy Cafe’s, Tom’s Urban, Nando’s, and Chipotle’s the corporate folks on work trips could want. National Harbor is only a ten-minute drive to D.C., so we spent some rainy afternoons at the various museums. My favorite was the Hirshhorn Art Museum. 

Then we trekked further north to a super cute and quaint little town called Cape May in southern-coastal New Jersey. The weather was pretty crisp and chilly for early April, but the town and beach are super cute and we loved it. We stayed in an Air BnB that was about a ten minute walk to the very cute downtown area, and our trip was filled with walks to cute bars and restaurants, perusing the shops, and exploring the vast, white-sand beaches of southern Jersey Shore. 

Roxbury, Boston, MA

Finally arriving in Boston, we settled into our Roxbury neighborhood, which sits next to Jamaica Plain and directly south of the main downtown area. Roxbury is one of Boston’s oldest neighborhoods, with a landscape and street pattern that predate much of the modern city. It appears on maps dating back to colonial New England, and its older streets and natural terrain give the neighborhood a character that feels distinctly different from downtown Boston. Although I really loved our neighborhood, it was certainly having a bit of a gentrification moment, with rents skyrocketing toward San Francisco prices. We were only a ten-minute walk from the Jackson Square T stop, Boston’s subway system, which meant we drove very sparingly. Driving in Boston is quite challenging, with narrow, winding streets, oddly wandering roads, and a city plan that clearly predates the invention of the motor vehicle.

An Interesting Metric for Enjoyment of a City

How often we turn Pebble on has become a surprising metric for how much we enjoy the city we are living in. One interesting way to look at this is through the iPhone Health app, which tracks your daily steps. For example, in New Orleans, I averaged about 8,100 steps a day. Well, Boston, to my surprise, came in at 8,353 steps per day during our first month there. Considering my height, that works out to almost four miles of walking every day.

Loving Boston

Our weekends were filled with train rides into Boston’s proper downtown neighborhoods, including the North End, Back Bay, and Beacon Hill, where we experienced the excellent food and drink scene, caught live music from Berklee students, and explored the ancient city streets. The Freedom Trail around Beacon Hill, Boston Common, and the North End was awe-inspiring, and I (controversially) don’t think there is a more beautiful park in the USA than Boston Common.

One of my favorite nights out was toward the end of our time in Boston. There was a World Cup game at Gillette Stadium where Scotland faced off against Haiti, and thousands of kilt-wearing Scots descended on the city. Paloma and I met up for dinner at the Union Oyster House, near Faneuil Hall and Haymarket, and found ourselves in the midst of the great beer drought of 2026. Several articles reported that the visiting Scots had contributed to the city completely running out of beer that night. I like to think we played a significant role in drinking our share.

We would also venture south of Roxbury to Jamaica Plain quite often, a quaint, tree-lined, park-filled neighborhood that reminded me a bit of Los Feliz in Los Angeles. It was slightly less dense than downtown, but full of beauty nonetheless. A beautiful linear park follows the train lines and would often host farmers markets, festivals, and other celebrations that we would stumble upon.

The main feature is Jamaica Pond, which has a beautiful mile-long loop around its perimeter and sits just off the neighborhood’s main street, Centre Street. We were about a mile and a half from this quaint stretch of Centre Street, and considering how often we walked there, that may explain our four-mile daily walking average. Jamaica Plain is also home to the Arnold Arboretum, which we visited several times to commune with nature and seek inspiration from the beautiful variety of tree species found there.

There was a beautiful park in our neighborhood called Franklin Park that reminded me a little of Golden Gate Park in San Francisco. Almost every day, Paloma and I would walk there and loop around the park, enjoying its beautiful trees and the serene escape it offered from the audible buzz of Roxbury.

Day Trips to Rockport, Salem, and Cape Cod

We took a day-trip to Salem to soak in all the witchy vibes, as well as explore a new coastal destination: Rockport. This is a beach town seated at the final stop of the commuter rail (essentially a Caltrain or Amtrak for the Boston metropolitan area) and has adorable shops and restaurants set between stacks of lobster pots and maritime ephemera. We grabbed an early dinner, some cocktails, and a couple of fun memorabilia t-shirts, including my “Sex, Drugs, and Lobster Rolls” shirt which would continue to be a hit all over New England. 

Provincetown (P-Town), located at the tip of Cape Cod, was also a beautiful addition to our day-trip itinerary during our Boston stay. We explored the numerous shops and restaurants in P-Town, and were floored by the beauty of this old coastal gem. Paloma and I stopped in Chatham to see her old family home, which was originally constructed in the 1700s, and remodeled during their time living there. Cape Cod has such a strong vibe, with its quaint coastal homes clad in grey cedar shakes and landscaped with blooming hydrangeas. 

Cons, If Any 

It’s hard to come up with the cons for Boston, as I fell hard in love with this city. However, the fact that there is an Airport really close by, and the city is as dense as it is, the noise and emissions pollution would be my main gripe. It is an expensive city by East Coast standards, however, from my Californian perspective, it is not the worst. By the end of our trip, my ears were ringing, my bank account was hurting, and my throat was scratchy, but ultimately, Boston is one of the most beautiful cities I’ve had the fortune of visiting and I hope to return as often as possible. 

-RoamingRushka