Boston may be one of the oldest cities in the United States. But, it continues to have this energetic pulse that makes it worth a fun weekend visit! I spent 36 hours exploring the city’s cobblestone streets, historic landmarks, and charming neighborhoods with my friend Megh. Between the Freedom Trail tour, the first tavern in the country, and a day trip to Salem, it was the perfect blend of history, food, and local flavor. It was on my bucket list to visit all cities in The Last of Us; after ten years, I finally checked it off with Boston!
Arrival & First Impressions
We arrived at HI Boston Hostel, located at 19 Stuart Street in Chinatown. It’s a modern hostel with a warm, social energy. The common areas are inviting, the rooms are comfortable with both private and dorm options, and the staff run a full slate of free activities including walking tours, welcome parties, and bike outings. HI Hostels are chains. I’ve stayed at their property in Reykjavik, Iceland, which also made this my first time staying in one in the US.
The beds were comfy, a bit creaky but nothing horrible, and the hostel provides towels and blankets for travelers. The rooms even had individual bathroom stalls, huge lockers, and bed curtains: things all backpackers know are hostel luxuries.
One of my favorite touches was the stack of journals in the front common area that had travelers’ messages, notes, stories, and inspiring words from around the world. There’s something so special about the uniquely humanistic, “I was here” momento. Near the reception area there were snacks, water bottles, locks, merchandise, and other needed items available for purchase. Of course, I got a sticker for my journal and patch for my backpack!
The hostel has the biggest communal kitchen I’ve seen. Plenty of space to cook, as well as pool tables, games, and cozy little nooks to get some work done. The location is also in walking distance to numerous great spots in the city. The hostel even partners with a nearby parking garage on Beach Street where you can get a discounted rate.
There’s also info spread throughout the hostel on infographics with things to do in the city. Most activities happen during the week. That was the only part of this hostel experience I wish was a bit different; there were no events on Saturday night. However, this HI does offer free Freedom Trail tours on Saturdays and Salem tours on Sundays!
At $110 a night, it was definitely the most expensive hostel I’ve stayed in lol. I’ve paid $10 a night in other countries with breakfast included. That being said, accommodations in the U.S. are pricier in general and staying at HI was much cheaper than hotels in Boston. It wasn’t my favorite hostel, but it was a good place to meet people and I’ll treasure them + our memories together forever. I’d say it’s more of a social hostel than a party hostel. Though, not as social as some of the ones I’ve stayed in throughout Central and South America.
Day 1: The Freedom Trail & Tavern Time
Morning start
After checking into the hostel, we kicked off Saturday with the free walking tour affiliated with the hostel at 11am, which is was the local “Freedom Trail” variant. Because HI Boston offers free walking tours and activities, you can join without fuss. Walking tours are one of the best ways to meet people in any hostel. Especially in Boston + if you’re solo traveling.
Our guide led us along the classic Freedom Trail path. Officially, the Freedom Trail is about 2.5 miles long, connecting 16 historic stops from Boston Common to Charlestown. The weather was PERFECT. High 70s and that perfect occasional breeze. I was expecting it to be a lot colder.
We passed the Massachusetts State House, Granary Burying Ground, King’s Chapel, the Old South Meeting House, the Old State House, Faneuil Hall, the Paul Revere House, and major historical sights. The red brick path makes it easy to follow, but having a guide brought stories, side details, and layers of meaning you don’t get just reading a guidebook.
I loved how walkable Boston is. Philly isn’t, so I always appreciate this component of new cities. The tour winds through leafy squares, narrow back alleys, and energetic neighborhoods, so you feel both part of the action and tucked into history. By mid-afternoon, my feet were feeling it. I should have brought better walking shoes; my feet ended up blistering lol so I’d recommend bringing a reliable pair of sneakers if you’re planning on doing these tours.
Tavern stop
At one point the tour paused at what the guide called the “first tavern in the states.” Boston has a few that claim historic precedence, notably the Union Oyster House and Bell in Hand Tavern. Sitting in a wooden-beam room, hearing the echoes of conversations past, sipping something simple. I noted how surreal it was to be in a space where revolutionaries might once have gathered.
North End & Italian flavors
Later the group wandered into the North End, Boston’s compact little Italian district. If you love food, this is the place. Brick row houses, narrow streets, restaurants with old signs, aromas of garlic and espresso. The North End is the perfect antidote to sightseeing fatigue: slow, delicious, and full of atmosphere. A few of the new friends we made on the walking tour ate at Lucida’s. Serving great Italian food, it was the first restaurant to bring authentic Italian cuisine to Boston! Be weary during the weekends. Lines for cannoli can be out the door!
Evening & Nightlife
I wouldn’t classify Boston as a huge “club city” in the traditional sense. The city’s charm lies in its taverns, pubs, cocktail lounges, and spots with live music or trivia nights. Nightclubs exist around the Theater District and Seaport, but the real nighttime joy is bar hopping in neighborhoods, catching conversations, and mellow late evenings. I felt safe walking in Boston at night. Granted, I was with a group, but I would have been more comfortable walking solo here than in other large cities I’ve been to.
We grabbed cocktails and beers, sat outside, and started sharing stories about how life in the U.S. felt different compared to Germany, the U.K., and Mexico. Even the little things were different such as bottle service, house party kickbacks, and the wild party culture in the U.K. One of our friends from the U.K. gave us a quick lesson in British slang, saying, “You can be a wanker, but he’s a twat,” and we spent a while laughing about their queuing culture.
I ordered the creamsicle mule, which sounded interesting. It was a tasty blend of absolut vanilla, triple sec, orange juice, and ginger beer! Our server was amazing and the food was exactly what we needed. It was so interesting to me to hear how people traveling internationally were comparing their country to the U.S, whereas it’s usually the other way around for me.
Later that night, our hostel group ventured to The Tam, a beloved dive bar located at 222 Tremont St. Established in the 1940s, The Tam has been a staple for locals seeking a no-frills drinking experience. With its vintage green awning and old-school Michelob Budweiser sign, it’s as recognizable an entrance as any Boston institution. Inside, the atmosphere is laid-back, offering affordable drinks and a welcoming environment for both regulars and newcomers. If I went to college here, I would have been hitting this place up regularly lol
I noticed how people dress in Boston. Both for going out and daily life, people tend to look a lot sharper than in Philly lol, which adds to the polished, relaxed energy of the bars and clubs. Kind of an odd observation, but one I found super interesting:)
Day 2: Salem Day Trip
Morning: Off to Salem
Sunday morning, Megh drove us north to Salem, a 30-40 minute ride from Boston. Salem leans into its witch trial history, but it also has a relaxed coastal character with colorful buildings, narrow streets, and historic architecture. There’s also a train to take and HI Hostel has Salem tours every Sunday at 11am. It was super nice to visit around Halloween! If you’re seeking a destination that blends history, culture, and Halloween magic, Salem is a must-visit. Its unique charm and festive atmosphere make it a standout choice for an October getaway.
In Salem I visited the Witch House (Judge Jonathan Corwin’s home), the Salem Witch Trials Memorial, and walked through streets that feel haunted in the gentlest, most charming way. The Salem Witch Museum also gives a theatrical, immersive recounting of the trials!
Around midday, we stopped at Red’s Sandwich Shop, a local fixture in Salem since 1945. Housed in the historic London Coffee House dating back to 1698, Red’s offers a cozy atmosphere where community and history mingle. It’s a bit hidden! I grabbed a breakfast sandwich that was super tasty. Red’s offers spooky seasonal coffee drinks and specials. Of course, I had to give it a try. Megh and I had a latte with peanut butter cold foam! Most people eat inside and might not know there’s takeout. Visitors can sit around the open kitchen area bar, which reminded me a lot of this diner called Sills in Layton, Utah!
Afterward, we explored the myriad Halloween shops lining the streets. From Spirit Halloween’s extensive costume selection to unique local boutiques, Salem’s shopping scene caters to all things spooky. Stores like Magic Parlor offer a range of jokes, gags, magic, make-up, and spiritual, new-age, and occult items.
The streets were alive with street artists showcasing their talents, adding to the city’s artistic flair. People donned creative costumes, embodying the Halloween spirit. We even participated in a free printmaking craft activity!
For those planning a visit, Salem’s Halloween festivities are part of the Haunted Happenings Festival, running throughout October. This internationally renowned celebration includes events like the Grand Parade, Howl-o-Ween Pet Parade, family film nights on Salem Common, costume balls, ghost tours, haunted houses, live music, and theatrical presentations.
Final Thoughts
Boston is charming in a way few cities manage. Historic without being frozen, lively without being chaotic, human-scaled without feeling small. In 36 hours I walked through centuries, ate deeply, and got a sense of the city’s cadence.
It’s a city built for foot traffic. For a weekend, you can see a lot in a short time and not feel regret for leaving behind access. Ideally, I think you only need a long weekend in Boston to feel satisfied with all it offers! There’s boat cruises, good eats, and a bunch of museums + sights sure to please any history buff.
As for nightlife, I’d sum it up like this: Boston doesn’t pulse like a club capital, but it has bar life. It’s about drinks, conversation, local energy, live music, and cozy late evenings more than all-night dance floors. I actually enjoyed that slower, more relaxed pace for once.
Salem was a perfect counterbalance: small town, witchy lore, and that warm surprise of finding a sandwich shop with history and flavor. I wasn’t expecting to go, but talking to other travelers in the hostel, they said it’s one of those things you just have to do.
Boston completely lived up to its reputation. The history, food, neighborhoods, and the walkable streets all came together to make a short weekend feel complete. Finishing my The Last of Us city bucket list here made the weekend feel like a personal accomplishment, and Boston delivered everything I was hoping for:)
Where The Wind Takes Me. 
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