RoamingRushka

June – July 2026

Boston was decidedly our last hoorah on the East Coast, having been in and around the Eastern Seaboard since Portland, ME starting in October 2024. So, in the middle of June 2026, we packed up Pebble and headed due west bound for Connecticut. I had driven through CT several times in this Eastern period, having roadtripped from Portland to CT for a work trip, and a couple of different times in Pebble to and from destinations, so my interest was always piqued as to what life was like in the massive suburb of NYC that is Connecticut. So I booked a Furnished Finder in Hartford; one of the cheapest stays we have had to date. 

Admittedly, our expectation for the month-and-half stay was that we would not actually be present in Hartford for much of that time. We had a music festival booked in near-by Greenfield, MA, a week-long family vacation planned in Kennebunkport, ME, and I had another week booked for a work trip to nearby-Shelton, CT as well. Additionally, we were hoping to visit friends who live a short drive away in NY, so Hartford was really just a convenient and cheap city to start our journey west and act as a centralized hub for our various excursions we had in mind. 

The first weekend of our stay in Hartford, we packed up and left for the Green River Music Festival in Greenfield, MA. Our favorite country artist, Charley Crockett was the headliner, and we were a fan of several of the other bands on the ticket, so it was a no-brainer. Greenfield is only about an hour north of Hartford, and the drive is stunning in the early summer, with the emerald flora fully immersing your experience on the road. The music festival was beautifully rural; placed in a green field surrounded by trees. We had seen Charley Crockett on this roadtrip previously, at Red Rocks in Colorado, so catching a Charley Crockett set in a beautiful backdrop is a recurring theme of our trip. 

After another beautiful country drive back, we settled into our new house in Hartford and got back into the rhythm of digital-nomad life. I was able to keep my gym membership from the Boston climbing gyms as the brand is the same, so naturally I spent a lot of my time at this climbing gym. The suburb, West Hartford, has cute restaurants and a lively main street, so we would go out to dinner there, and walk around some of the river walks that the quaint suburb had to offer. 

Soon after our first week of living in Hartford, we had another vacation to attend to, this time in Maine. Paloma’s mom, stepdad, and siblings take a vacation in the early summer on a yearly cadence; usually in Europe, but always in a very fancy and nice Air BnB. The Maine trip was the American equivalent in Kennebunkport, Maine, about an hour south of Portland. The house we stayed in was originally built in the 1700s, and was less than a ten minute walk to the main downtown artery, loaded with shops, restaurants, and wandering tourists. 

Coastal Southern Maine is a vacationer’s paradise; there’s a reason Maine is known as Vacationland. The town of Ogunquit, which is about fifteen minutes south of Kennebunkport by car, was the first town I had experienced in Maine. Paloma and I stayed here for a few nights before our FurnishedFinder booking in Portland, for Paloma’s birthday. October was the start of the off-season in Vacationland, so the town of Ogunquit was fairly empty, but the restaurants were still open. I look back on this Autumn, 2024 vacation with such fondness, considering this was the start of our digital-nomad life, and the first real goal (arriving to the east coast by autumn) that we could check off our list. Yes, the leaves were all bright orange and yellow, and the air was crisp; feel free to check out one of my first blog entries about this time here. 

This time, our trip was in late-June, so the peak of the vacation season. The weather was perfect, always around the mid to low-seventies, and we only had a couple moments of rain. The vacationers were out in full swing, presenting a much livelier atmosphere than our first visit in October years prior. It was so nice to be with Paloma’s family; chock full of great conversations, meals, walks, boatrides, sight seeing, and even an off-broadway play. Finally, after a lovely week, we got back in Pebble and made the three-hour drive back to Hartford. 

Soon enough, it was the 250th independence day, also known as the semisesquicentennial (definitely spelled correctly on my first try). We decided to make the most of it and visit my old roommates in their new city by Beacon, NY, which is only about an hour and half drive away from Hartford.

It was great to catch up with old friends, and visit this adorable town which is a train ride away from NYC making it a weekend destination for folks in the Big Apple. Unfortunately, there was a torrential downpour as evening struck on the 4th, so no fireworks were visible aside from the flashes of light illuminating the stormclouds. I thought that the sounds of gunpowder and subtle flashes of light in the storm were actually a much more realistic portrayal of an independence battle anyway. 

We took another day-trip from Hartford that was worth noting. Mystic, CT, known for the movie Mystic Pizza with Julia Roberts, was about a 45-minute drive from our house, and made a wonderful daytrip. Surprisingly similar to Kennebunkport, ME, Mystic has a beautiful downtown artery filled to the brim with adorable shops, restaurants, and pubs. We walked all around, shopped for souvenirs, and even ventured to another quaint town nearby called Stonington. Although one might think to get pizza at Mystic Pizza, made famous by Julia Roberts, the locals warned that it is indeed a tourist trap as we feared. The trip to Stonington yielded great pizza at The Back Door Kitchen & Pizzeria. These quintessential coastal Connecticut conurbations invoke such a strong vacation feeling.   

Aside from the various road trips we took, Hartford was at best a fairly unremarkable city, and at worst, an impoverished slurb (slum-suburb). We were excited to hit the road when we finally packed up Pebble with Motor City in our sights. 

-RoamingRushka