A 6 a.m. flight had us landing in Boston around 10 a.m. This was not a typical vacation for us, but rather, a cousin’s wedding weekend turned vacation, and thus, we were with family. Mom, Dad, Ty, Theresa, Anthony, myself, and all of our luggage squeezed into a Volkswagen Atlas rental, and we hit the road out to the Berkshires.
Traffic slowed us down, but we made it to the Berkshires – specifically, Great Barrington – by early afternoon. We had a couple hours to kill, so we wandered downtown checking out what the town had to offer, and ended up stopping in a Mexican restaurant for a margarita. As we were getting ready to leave, a torrential downpour began. We waited it out until it calmed slightly, and then ran back to our hotel, myself in sandals, margarita sloshing around my stomach.
The rain came back in force while we got ready for that evening’s rehearsal dinner party. The parking lot was flooded, and we were all trying to figure out how we would get to our shuttle without getting soaked in our nice dress clothes. After an hour delay, the rain let up.
The shuttle took us to Taft Farms. Unfortunately, the floods made getting out to the field to where the tents were quite difficult. Buses were getting stuck in mud. Tractors eventually had to come out to grab the rest of the guests. Nevertheless, the party was beautiful, the wine was flowing, and dinner was great.
It was after 1 a.m. when we caught the last tractor/shuttle combo back to our hotel. I was with it enough to know to chug some water and take some aspirin before bed… and then chug more water throughout the night… and take more aspirin in the morning… but still, ended up with about the worst hangover I’ve ever had somehow.
I was not sure I’d survive the day outside of bed, but Anthony convinced me to attempt a hike since it was our one opportunity. He and I, my brother and soon-to-be sister-in-law, and my cousin hopped in the car and drove the 10 minutes to Monument Mountain.
I started sweating out the alcohol as we climbed, and the fresh air soothed me. The further we got up that mountain, the more my hangover melted away.
We finally got to the top, and the clouds had lifted enough to offer wide views of the hills of the Berkshires around us.
It was a hot, humid day, so we sat there awhile catching our breath and hoping for a breeze.
We climbed down a few rocks, and the view on the other side of the mountain presented itself as well.
We had a pretty steep descent the whole way down and back to the parking lot, but it was broken up with a stop at a small waterfall that I’m not sure would have existed if it weren’t for the floods the night before.
A big, delicious pizza and salad lunch and a short brief nap further refreshed me, and then it was time to get ready for the wedding.
Sunny skies welcomed us this time, to Konkapot Bottoms, a family estate of the bride. We grabbed a glass of iced tea and made our way to the clearing in the cornfield for the ceremony.
After, we crossed the street to cocktail hour, snacking on hors d’oeuvres, sipping the specialty wedding cocktails, exploring the property.
We weren’t out there long before it was time to join the main party in the big tent. We found our assigned seats, enjoyed the large band, and ate way too much food.
Somehow, I got talked into a tequila shot, taken from champagne glasses, and after that, I spent the evening on the dance floor.
After awhile, the band packed up and was replaced by a DJ for us late night partiers. Pizza was brought out, but I was far too full to partake. Eventually, my feet were tired, and I ventured outside to the firepit, where I cozied up under a nice flannel blanket for a nap.
We caught the last shuttle back to the hotel at 2:30 a.m. and before we knew it, it was time to wake up and get ready. We loaded up the car and drove to Wheatleigh Hotel for brunch, which was absolutely stunning. Anthony and I took a walk around the property, checking out the various gardens and greenery.
We filled our bellies and said goodbye to aunts, uncles, cousins.
It was afternoon when we made it back to Boston and dropped off our rental car. We grabbed a couple Ubers to our hotel, the Colonnade on Beacon Hill.
We were exhausted, so we had a chill evening of dinner, walking down Newbury St., and checking out our rooftop pool.
And speaking of said pool, Ty and Theresa were staying in a room right underneath it which ended up with water gushing through the ceiling onto all of their stuff. Fortunately, the hotel took care of the dry-cleaning and gave them some money to buy some clothes for that night and the next day. They got moved to a top floor room, and all was well.
The following morning we walked through the neighborhoods behind the hotel and ate some breakfast.
After, we went to Faneuil Hall to start our walking tour of the Freedom Trail. Our guide was in full dress, despite the 95 degree weather outside. She did a wonderful job of staying in character, making her audience laugh, and giving us all the historical information we needed to know.
Probably my favorite part of the tour was the Granary burying ground by King’s Chapel, where John Hancock and Paul Revere were buried, and Samuel Adams is commemorated.
We ended at Boston Common, and from there, Anthony and I headed to the harbor area to walk around and eat some lunch.
We went on a long walk from there back through town to check out the Cheers bar. It was packed inside, so we basically took enough time to snap a couple pictures, and head back out.
We walked through the Public Garden, which dazzled with the blue skies above and the buildings around. I imagined living in Boston, and coming here on nice weekend mornings with a picnic brunch.
Some more walking and we ended up at our hotel, where we went up to the pool to cool off.
We got ready and ventured back out, first top the public library. I started feeling sick, and we sat out in the courtyard.
I rested there in the shade, progressively feeling worse and worse. I knew I wasn’t feeling up to doing anything else, but I was scared to leave the library and walk back to the hotel because of how nauseous I felt. I finally worked up the nerve, and as soon as we made it back to our room, I was done for. I spent the rest of the night lying on the bathroom floor, fighting food poisoning (I’m guessing), trying to sip gatorade to prevent an emergency room visit.
Fortunately, it was just the one night that was a waste. I woke up the next morning feeling much better. So much better, in fact, that I decided to spend the whole morning on a boat out at sea.
We had an hour and a half ride out to the feeding area for whales, but halfway there, we slowed down to see a nursery pod of dolphins following alongside the boat. There were dozens of them, and of course, they brought a smile to every single person on that boat.
Once we made it to our final destination, everyone came out onto the deck, craning their necks for a site of a whale. After a few minutes, we saw a whale tail in the distance.
Soon enough, we were basically surrounded by humpback whales. One came right up close to the boat.
And then a mother and a calf came over as well.
We saw tail after tail after tail.
But a tiny boat nearby had the best show.
At one point, a whale was kick feeding, and just as she was about to come up through the bubbles, another whale swooped in and stole the fruits of her labor, all just two feet from the little boat.
Our last good site was of a mouth wide open, scooping up some fish, and then we turned back.
The ride back was lovely as well, gliding by the lighthouse, and then the Boston skyline coming more and more into view.
We grabbed some salad for lunch and then met back up with my parents. I was staying an extra night for a work office visit while I was in town, so I said goodbye to my family and Anthony, and I checked into my new hotel, Boston Park Plaza, which had a wonderful view from the room.
I wasted no timing in getting some more steps in, walking back through the public garden.
I crossed a footbridge and ended up at Charles River Esplanade, which was a fantastic place to hang out and another site that I imagined frequenting if I lived there.
It was another hot day for Boston, but people were running and biking along the trails. Others sat on the dock on the water, and still more peppered the park benches.
I sat down on a bench myself, watching people paddle through the water, geese swimming next to them.
I spent a long while there, but I eventually decided I needed to eat some dinner and get back to the hotel to get ready for the next day.
I walked along Beacon St, enjoying the architecture.
I walked past some lovely green spaces and the beautiful Church of the Covenant before finally picking somewhere for dinner.
That evening and the next day passed by quickly, and after some flight delays and excitement at the airport, I was on my way home. I spent a decent chunk of this trip fairly miserable, but even still, I enjoyed myself immensely and would certainly consider moving to this part of the country someday.