Boston in the Fall

I’d always planned to visit Boston as part of a Northeast Fall foliage road trip in addition to visiting other New England states. I was given the opportunity to visit Boston this Fall for a long weekend, sans the road trip, and I am so glad I was able to get a small sample of what Boston has to offer.

I landed at Boston Logan Airport and took the Silver Line Bus, which is free to pick up at the airport. We stayed at the Omni Boston Hotel at the Seaport, so the bus ride was only 3 stops away. Omni is such a beautiful property with a ton of amenities, city and water views, and is across the street from Boston’s convention center. Watch my hotel tour on YouTube below.

Once I settled in, I walked to Blank Street coffee for a matcha latte as there are only a few locations across London, New York, D.C. and Boston. I’d only heard of Blank Street due to @melissawardrobe having a matcha collab with the coffee shop. Unfortunately, Mel’s maple matcha was only available at their London and New York locations, and Blank Street doesnt normally stock maple syrup, so I ordered a makeshift Mel’s matcha — their regular matcha latte with vanilla syrup and cinnamon, which was pretty good.

Because we were only staying in town for a few days and didn’t plan to venture out of the city, we didn’t rent a car. Boston is very walkable, with good public transportation and rideshares are plentiful and affordable. From Blank Street, I took a Lyft to Heritage Club Boston Dispensary, a black-owned dispensary in Charlestown. I picked up a few pre-roll goodies and headed back to Omni to meet my friend to start our evening.

Our main reason for going to Boston was to attend a pre-season Celtics game. The game was in October, and we bought tickets in August. In August most of the seats were already sold out, so we had to purchase from a third-party resale site. Once we arrived to the game, it was sold out, likely because the Celtics made it to last year’s semi-finals. We purchased really great seats in Loge 18 so we were able to see the Celtics come out of the tunnel. Unfortunately for this pre-season game, star Jayson Tatum did not play along with many other openers. This game was moreso for rookies. I found the TD Stadium to be very modern compared to other arenas I’ve visited. There are a lot of self-checkout convenience shops with pay-and-go technology, a few bars, and a Frito Lay test kitchen. We were able to buy a full bottle of wine to enjoy during the game.

Initially, we had reservations for dinner at Contessa on Newbury Street after the game, but we missed our reservation. In the early planning stage of this Boston trip, a lot of vlogs and social media recommendations pointed us to Contessa noting it was the best Italian restaurant in Boston. I found it interesting because when you come to Chicago, you can ask 20 people for Italian restaurant recommendations and you’d receive 20+ different recommendations on what people thought was the best. Because we missed our reservation, and by the time we arrived to Contessa, the kitchen was closed so the hostess offered to sit us at the bar to order drinks. We were able to regroup and decide to have dinner at Lucca in North End. Lucca focuses on North Italian cuisine, and we found the restaurant very family-forward. The manager sat and talked with us for almost our entire time there and made us feel very welcomed.

We started day 2 by having breakfast at Tatte, which is a chain bakery and cafe with multiple locations across Massachusetts and D.C. I ordered their lemon poppy cake slice and American breakfast. My friend ordered the shakshuka and a coffee. Everything that we had was delicious. They sell breakfast and lunch plates, pastries, salads, and sandwiches. When we visited, the restaurant was busy and we had to wait a few minutes for a seat at the coffee bar. If you dont have time to sit down to eat breakfast or lunch, Tatte is also great to grab a pastry and beverage.

After breakfast, we hopped on Boston’s city bus to start the Freedom Trail. We purchased a public transit day-pass for $11 at the station. We didn’t book a tour guide for the Freedom Trail since it’s free, but I did use the National Park Services free audio-guided tour. We saw other people on the trail on private and group tours, and some purchased apps for the audio tour. Boston’s Freedom Trail is almost 2.5 miles long passing along 16 historic sites that helped to shape American history. The Trail is for pedestrians showcasing churches, burial grounds, historic markers, and government buildings. Along the trail, you’ll see 2 vertical red bricks centered between grey bricks and perpendicular to other red bricks. The Freedom Trail begins in the Boston Common, accessible by the Park Street train station. The Boston Common is the oldest park in the U.S. and houses the monument of Robert Shaw and Massachusetts 54th Regiment Memorial commemorating one of the first African American regiments of the Civil War.

Through the Freedom Trail I realized I missed a lot of American History in school, but found it quite fascinating that this history was so freely accessible in a city, and not clouded by a museum or private entity.
Along the Freedom Trail we stopped at the Massachusetts State House which is still in operation today (housing the state Senate, House of Representatives, and Governor’s office), Park Street Church, and Granary Burying Ground, one of Boston’s oldest cemeteries — the resting place of Paul Revere, Sam Adams, John Hancock, victims of the Boston Massacre, and 5,000 others.

King’s Chapel was probably one of the most insightful stops on the tour for me. The church began because James II asked his brother Charles to establish the Dominion of New England to unite the American colonies and strengthen English control over the colony, establishing his legitimacy as king. A Reverand Radcliffe was tasked with presiding over the church but faced opposition from Bostonians as they were predominantly Puritans at the time. Puritan landowners refused to offer land to the king, his brother, or the Reverand for their church, so the local government stepped in, seizing public burial grounds and granting it to the church. The church was originally wooden when it was built in the 1600s, in its current location. In the 1800s a stone structure was built around the wooden frame, and once the stone structure was complete, the wooden frame was dismantled. The church still holds Sunday services today and has some of the original features including granite columns, the original 10 commandments, The Lord’s Prayer, and houses one of the tallest pulpits. Unlike modern church pews, King’s Chapel has boxes with swing doors for congregants so individuals and families were able to purchase their own boxes and have assigned seats during weekly service. Because there was no cooling or heating systems centuries ago, huddling in these boxes was the norm. Churchgoers who were well off paid more money to sit in the front closer to the Reverand and commoners were able to sit further in the back.

We kept following the bricks and listening to NPS when it lead us to the site of the First Pubic School Site, Boston Latin School. Erected in the 1600s, the first public school in the U.S. was a wooden structure that educated John Hancock and Sam Adams, and many other men to prepare them for admission to Harvard. Ben Franklin attended The Latin School for 2 years until his family couldn’t afford to send him anymore. A mosaic on the sidewalk commemorates the original site of the school, along with a statue of Ben Franklin behind the gate which is now Boston’s Old City Hall and a Ruth’s Chris Steak House.

As we kept walking, we stumbled upon a year-round Christmas store, Old Corner Christmas Store: I had to stop in to see what they had! There were a ton of Christmas ornaments donning Boston Celitcs, rainbows, leprechauns, and traditional Christmas gear. I purchased a lobster roll Christmas ornament because you cant get more Boston than that! Along Washington Street, we saw a lot of jewelry stores and shops like TJ Maxx, Home Goods, and Old Navy so we had to take a quick detour to check those out. We were then back on the Trail and went to The Old State House. Most stops along the Freedom Tour are free entry or ask for a nominal donation. Other sites such as The Old State House require paid admission for entry or a tour. We were able to enter The Old State House, but were only permitted to look around the gift shop without purchasing an admission ticket. Outside of The Old State House is a cobblestone sidewalk commemoration of the Boston Massacre. The actual site of the Boston Massacre where 5 people lost their lives is now a downtown Boston Street.

As we continued to follow the cobblestone to Faneuil Hall, we saw a Sam Adams Taproom. My friend and I stopped in to see what it was all about. I’m not a beer girlie at all, but I do things for the plot. There are only 2 Sam Adams Taprooms in the U.S. with the other being in Cincinnati. The Taproom does not take reservations and is a pretty expansive place with 2 bars, and picnic table seating throughout. There is a kitchen serving bar food, counter-service style. We ordered a custom flight of 4 for $17. My friend ordered the Boston Lager, seasonal/rotational peach apricot IPA. I on the other hand stuck to my roots with a Truly Berry, which I didn’t find strong at all (only 5% ABV) but very light, crisp, and refreshing… a good Summer drink. I did venture out a bit by trying the cherry wheat. It was more tart cherry-forward than beer-heavy. If I had to, I would order a cherry wheat beer at a baseball game, so I find that to be real progress!

Our bartender at the Taproom was so sweet and knowledgeable. She walked us through their menu, gave great recommendations on each of our preferences, and had great insights into how the Taproom operates. I would recommend Sam Adams as a stop on the Freedom Tour, or in general while you’re in Boston. We initially had plans to have lunch at Quincy Market and to pick up a clam chowder. Our waitress advised against it and said the best clam chowder is at Union Oyster House. So, we obviously had to detour and listen to a local’s recommendation. Reservations are recommended at Union Oyster House as the restaurant isn’t large, and fills up quickly. We were able to snag 2 seats at the bar after being quoted a 45-minute wait. We only ordered a bowl of clam chowder and a few cocktails. The clam chowder is out of this world and made me realize I’ve never had proper chowder before! It was seasoned, flavorful, and had big clam pieces and perfectly soft potato chunks in the soup. A couple next to us ordered the chowder as well as a lobster roll, which looked equally delicious and had us debating if we needed a roll. Unfortunately, we passed as to not ruin our appetite for dinner. I can’t attest to their lobster roll, but Union Oyster House has the best clam chowder hands down. Again, the staff from the hostess stand to the bartenders were so hospitable and answered all of our questions.

After lunch, we were a bit over the Freedom Trail, and planned to call it a day from there. We hopped back on the Green Line train and headed to Newbury Street to window shop. I’ve taken public transit in many cities, but I think Boston’s subway system may take some time for me to understand. The Green Line basically operates over 5 lines, so you have to be careful to take the right Green Line train in the right direction. When I first saw it, it took me by surprise.

Newbury is a Back Bay street lined with boutique shops, national brands, and high-end stores like Hermes, Chanel, Brunello Cucinelli, and more. Newbury is akin to Georgetown in D.C. or Harajuku in Tokyo in my opinion. We didn’t do any shopping on Newbury as we still had the rest of the day ahead of us, and were trying to travel light.

From Newbury, we walked through Boston’s Public Garden to get to Acorn Street in the Beacon Hill neighborhood. Acorn Street is a residential, cobblestone street that is an up-hill trek that you’ve probably seen over social media. Once we arrived, many other people had the same idea as us to take photos in the alley of the picturesque New England background. We took a few photos and were pretty tired of walking by this point and decided to rest with the sightseeing.

Front photo of Quincy Market in Boston, MA on Freedom Trail

Because we were so close to finishing the trail, I headed back to Quincy Market just to see what I had missed for lunch. Quincy Market is a food hall that is quintessential for groups, picky eaters, people on the go, or anyone wanting a quick bite. There are several vendors selling lobster rolls, lobster mac and cheese, clam chowder, Italian food, pasta, pizza, Chinese food, and desserts. There are also vendors on the exterior of the food hall selling crafts and souvenirs. Across the walkway from Quincy Market is Faneuil Hall which is not food-focused, but artisan and craft-focused with vendors selling art, crafts, clothing, seasonings, kitchen supplies, and souvenirs. I was moving along the trail leaving Faneuil and it started to pour down rain so I had to call it quits, but not before I grabbed a sweet treat. I saw that I wasn’t too far away from Little Italy and many prominent cannoli spots. In the rain, I stood in line for almost 20 minutes at Mike’s Pastry until I realized they are a cash-only establishment and I had no cash on me! There were so many people walking up and down the street with their white cannoli boxes and I was sad that I wouldn’t be able to try a cannoli that night! I quickly Googled nearby cannoli spots and found Bova’s Bakery was the next block over — they accept card payments and are open 24/7. Once I walked in to Bova’s it had a corner store vibe and the employees are eager to get you in and out. It was in the evening, so they were out of a few cannoli flavors, but they do have a fairly extensive Italian bakery selection including lemon squares, cheesecake slices, tiramisu Boston Creme Pies, Italian cookies, zeppoles, lobster tails, whoopie pies, cupcakes, and pies by the slice or whole. In addition to sweet Italian treats, Bova sells savory options including pizza slices, subs, calzones, and arancini. Although they were out of flavors that I wanted to try, I can say that I tried my first cannolis in Boston — I had their traditional and pistachio filling. I think that eating one cannoli is fine, but I found the filling to be very sweet and dense.

I had dessert before dinner, but that’s okay because it was finally our redemption day to finally have Contessa. The hostess was kind enough to rebook our reservation that we missed to the next day, and we were NOT going to miss this reservation. We started off with the meatballs aldo and tonnato crudo. I debated between the meatballs and burrata as my starter because while both are basic and can be found on almost every Italian menu, you cant go wrong with the basics. My waitress recommended the meatballs because they’re made with veal, ground pork, and bacon then topped with pickled onions and a mustard seed sauce which is a far cry from the traditional marinara sauce and parmesan. My friend and I shared their signature spicy lobster Capellini pasta as an entree, and it was delicious. Was the meal service top tier? Yes. Was the food amazing? Yes. Did I leave full after spending $150 including cocktails? No.
In my opinion, Contessa is all about the vibes and experience. The food was good, but the aesthetic was better. At night the restaurant is moody, sexy, dim, and feels exclusive.

Now that we had fuel after dinner, we weren’t ready to call it a night just yet. We tried to bar hop but could not find a lounge or club open on a Sunday. We thought we came prepared with a list of lounges and clubs to visit, but they were not open due to it being a Sunday or due to it being a holiday weekend. We searched for bars in the area and found a few that were still serving drinks, but not playing any music, or were playing music and had drinks, but were not playing the right music for us, or did not have people dancing. We hopped from Lyft to Lyft going from one spot to the next and seeking recommendations for at least 2 hours before calling it a night. The locals gave us the consensus that Boston is not a party town unless you’re in college, and if so, you need to go to closer to the universities to party. I’m not a heavy partier or someone who likes to go out frequently, but I found it interesting that we could not find a single place for a night cap in the city that played good music with drinks and had a good vibe. If anyone has recommendations on clubs or lounges that serve cocktails and plays hip-hop/ R&B in Boston, please let me know in the comments below so I know where to go next time.

From day 2 in Boston, I realized I didn’t know as much American History as I should. I booked a ticket at Boston Tea Party Ship & Museum for my third day in Boston. The Tea Party & Museum is within walking distance from Seaport, located on the Boston Harbor. The experience starts with all guests sitting in City Hall with reenactment actors performing, how the Boston Tea Party started. We were all given playing cards representing some notable people and townspeople. All of the actors performed really well and dressed the part. The actors asked for volunteers to have small parts in the reenactment, which were at most 4-5 lines. The dialogue was to resemble all attendees being back in Boston’s City Hall when the city got word that they would be taxed on tea from England without having representation in Parliament, and we planned anarchy on how we would retaliate.

After the reenactment, we were then able to tour the ship and push tea overboard. Boston Tea Party Ship & Museum’s boat is not too far away from the original Boston Tea Party location. The actors told me that the original location of the Boston Tea Party was on the shore of where the Intercontinental Hotel now sits, which is across the harbor.

Sharett from Cheap Thrills Blog at The Boston Tea Party & Museum reenacting throwing tea overboard

The entire experience takes maybe an hour, then you’re released to the gift shop and bakery. Forewarning: while the scones and baked goods from the bakery may smell delicious as they’re baking, the scones are terrible so do not waste your money on them. I purchased a sweet and savory scone, and there was no taste in either scone, so you can definitely pass on that impulse buy.
On the souvenir front, there are many souvenirs here that I did not find elsewhere in Boston along with a variety of teas, ceramics, and other trinkets.

After the tea party reenactment, my friend and I had lunch at Boston Sail Loft. This restaurant will also be a skip for me. Union Oyster House has the best clam chowder that I’ve had, but I wanted to try what other restaurants offered before I made such a grand claim — I ordered a bowl of clam chowder here at Boston Sail Loft, and while it was not terrible, it was not better than Union Oyster House. Boston Sail Loft‘s clam chowder flavor was not as pronounced and the clams weren’t as big. Because I still hadn’t gotten a lobster roll in Boston I had to try one on my last day. I am not a big boiled lobster fan, so I may be biased. The roll here was full of lobster meat, but the lobster lacked flavor. I figured the lobster would just be boiled and served with butter, so I asked for Old Bay to season my roll — the seasoning never came. Boston Sail Loft is situated on the water, so it does provide a beautiful view of the boats and water. Other than that, I don’t think its much to write home about.
After lunch, we walked around the area for a bit then wondered, why not take a ferry?! The first ferry ticket station we found was going too far away and the ticket agent recommended we buy a ticket for the Charlestown ferry if we only wanted to get on a boat with no clear destination in mind. The Charlestown ferry dropped us off at the Charlestown Navy Yard and we walked around a bit, but were moreso enthralled by being on the water. The roundtrip ride on the ferry, walking around the Navy Yard, and back took roughly an hour, and the views on the water alone are worth the trip.

By this time, it was finally time for us to head to the airport to end our Boston adventure. All in all, I enjoyed Boston even though we didn’t have the best weather every day. Three days was just enough time to get our bearings and a lay of the land and realize I need to come back. There are still so many things I didn’t get a chance to experience, and restaurants I have not tried. So hopefully I will be back for baseball season, or for my Northeast Fall foliage road trip.

Is there anything specific that you think I should do the next time I’m in Boston?? If so, let me know below in the comments.