A Guide to Boston

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Boston is a city of many firsts – home to the first American public park, first American college, first American subway, first American newspaper, and many more. But what stood out to me was how it is the perfect city for a weekend getaway.

Just a 3.5 hour drive from NYC without traffic (with traffic it can easily take 5+ hours), it is a very walkable city with lots to discover on Shabbos and just the right amount of activities for Friday and Sunday. We chose Boston for precisely this reason, but decided against ‘covering’ the city and instead took it at a very relaxed pace. In the guide below, I will include both the things we did as well as the ones we would’ve liked to. Please share any related personal experiences in the comments to help in future trips.

Background Info

Known as the home of the American revolution, Boston is steeped in American history. Some of the first revolts started here with the Boston massacre and Boston Tea Party. The battles of Lexington & Concord (which started the Revolutionary War) and Bunker Hill are also right near Boston and revolved around gaining the upper hand in Boston. There are many historical sites in and around Boston and you can feel American pride everywhere in the city.

The greater Boston area is also home to many of the most prestigious American colleges including Harvard and MIT. Because of this, the city is full of students and graduates. Many of the best hospitals area also centered in Boston. All of this makes Boston a hub of technology and business – and traffic and hipsters by association.

Another interesting fact about Boston is that it is mainly a landfilled city. The original historical Boston fought over by the loyalists and patriots was a small peninsula jutting into the Boston Harbor. Over the years, the marshes around Boston were filled and the city was literally expanded. Modern Boston is about 50% larger in land area than in colonial times.

Transportation

Boston is notorious for its terrible traffic and no parking. If possible, it is recommended to rely on public transportation, or even bikes to get around. Sunday parking is free, but during the week most places are parking by permit only and garages charge $40/night on average. If staying in a hotel, check if they have a deal with a garage for a discount.

The ‘T’ – their subway system – is supposed to be very easy to use and well connected and they also have a good bus and light rail system. Since we did drive up, we had our car with us and didn’t try out local transportation.

Kosher Food

There is a big Jewish community in Brookline – about 20 min from Downtown Boston. There are many shuls and restaurants there as well as a supermarket. There are also a few more smaller suburbs in the surrounding area with a Jewish presence.

The local hechsher KVH is considered acceptable according to the CRC. Most of the dairy restaurants are not Cholov Yisroel unless specified otherwise. The following list is NOT exhaustive. You can find more options on the KVH website or Chabad website (which includes restaurants from other certifications not necessarily on the CRC list – as always confirm with your LOR about different hechsherim).

• The Butcherie
  A supermarket offering groceries such as meat, baked goods & prepared food, plus wine, as well as a takeout.
  428 Harvard St, Brookline, MA 02446
• Kupel’s Bakery
  Kosher bakery drawing crowds with ample bagel flavors & spreads, plus pastries such as bear claws.
  421 Harvard Street, Brookline, MA 02446
• Pure Cold Press – Cholov Yisroel
  Chill, California-vibe counter-serve spot offering cold-pressed juices, veggie sandwiches & more.
  326 Harvard St, Brookline, MA 02446
• Veggie Crust – Cholov Yisroel
  Indian vegetarian spot. This is a non-Jewish chain with only two of their locations being Kosher – the one in Brookline and the one in Waltham-Watertown.
  8 Cypress St, Brookline, MA 02445
  14 Warren St, Waltham, MA 02453
• ZA’TAR Mediterranean Cuisine
  Offering exceptional Mediterranean cuisine with fresh, high-quality ingredients including flavorful falafel pita, perfectly seasoned chicken grill, and mouthwatering desserts like Baklava
  10 Cypress St, Brookline, MA 02445
• Rami’s
  Counter-serve eatery in a basic space serving falafel, shawarma & other kosher Middle Eastern fare.
  324 Harvard St, Brookline, MA 02446
• Zayde’s Market
  Bakery – In Store, Butcher, Catering, Groceries, Light Food Service, Takeout Counter
  Pizza is strictly Cholov Yisroel and Pas Yisroel.
  15 Washington St, Canton, MA 02021

We only had a chance to try Pure Cold Press for a late brunch on Sunday. The food was fresh, delicious and hit the spot. The service was amazing and the space was full but not packed. Highly recommend for breakfast or lunch.

Accommodation

Since we wanted this trip to cost us minimally out of pocket, we booked our hotel with Chase points. Based on our budget, we had narrowed our options down to Pennyweight Hotel Boston, Curio Collection by Hilton or The Revolution Hotel. The latter spoke to us right away. We loved the decor, the reviews were amazing and raved about the cleanliness and service which are the two most important things to us when traveling. But – and this is a big but – it has shared bathrooms. They do have rooms with bathrooms, but the rooms within our budget had ‘bathroom down the hall’. It is basically about 4 – 6 shared bathrooms (shower and toilet) for every 8 – 12 rooms. They clean the bathrooms between every use (there’s a card to flip over to notify them that the room needs attention) and they do keep it very meticulous. At last we decided to be brave and try it out. Since we were gonna try camping for our first time on the following Sunday, it felt like a nice way to ease into it. Our stay was truly amazing and worked out great. Since the toilets on our floor were automated, we needed to use the downstairs toilets on Shabbos, but the hotel staff was extremely accommodating and gave us a low floor room and showed us the stairs for easy access. The front door was automated and needed some coordinating to make sure we didn’t turn it on (it runs on a very long delay once open, so it wasn’t so much of a problem). There is a back door for exiting and we didn’t get to double check, but it could be possible to enter via the restaurant when it it open to avoid the automatic doors. The location was also amazing as it is just an 8 minute walk from Chabad in a nice but quiet neighborhood. While I acknowledge that this is not for everyone, we loved our stay there.

For the doors my husband made this beautifully simple contraption of a card taped to the wall. When the card was down, the door wouldn’t lock (but would look fully closed from outside) and when we were inside and wanted the door locked we just flipped it up.

Activities

• Boston Tea Party Ships & Museum
  A fun, interactive reenactment of the Boston tea party on a floating history museum with multimedia exhibits & a tearoom.
  Fun for all ages. Tickets sell out early.
  
• Freedom Trail
  2.5-mile route with historic sites, including the Boston Commons – America’s oldest public park, Paul Revere’s House, the old Statehouse (in front of which the Boston Massacre happened), Granary Burying Ground (Paul Revere and Samuel Adams’ resting place), and more. Some of the stops now house museums which you can enter.
  You can do this as a self guided tour. There is a red brick marking on the floor to follow along. But if you’d like to learn about the American history and the stories behind the stops, a good tour guide will make it all the more interesting.
  
• JFK Presidential Library
  Celebrate the life and legacy of America’s 35th president JFK. Overlooking Boston Harbor, it features exhibits on Kennedy’s presidency, the space race, the Peace Corps, and Jacqueline Kennedy’s role in the White House. Visitors can explore artifacts, films, and interactive displays that bring the 1960s to life in an inspiring waterfront setting.
  
• USS Constitution
  The USS Constitution, known as “Old Ironsides,” is the world’s oldest commissioned warship still afloat, launched in 1797 and made famous during the War of 1812. Visitors can walk the decks, see the massive cannons, and meet active-duty Navy sailors who serve as the ship’s crew. Right next door, the USS Constitution Museum brings the ship’s history to life with interactive exhibits, hands-on activities for kids (like “sail a ship” or “fire a cannon”), and artifacts from the early U.S. Navy. Together, the ship and museum offer a unique chance to step back into America’s maritime past.
  
• MIT Museum
  A museum focusing on the accomplishments at MIT including some interactive exhibits, an exhibit on AI, genetic engineering and other interesting sciences. The museum is interesting for anyone interested in the advancement of science but not necessarily entertaining for kids or anyone only mildly interested.

• Harvard Museum of Natural History
  Extensive natural-science collections, including animals, minerals & a famous Glass Flower exhibition which is supposed to be something spectacular.
  
• Museum of Science
  Visitors can explore hands-on science experiments, watch electricity spark in the Theater of Electricity, see live animal presentations, and catch shows at the Charles Hayden Planetarium or Mugar Omni Theater. It’s a fun mix of learning and discovery for all ages, right on the banks of the Charles River. Unlike the MIT museum this is a little more fun and generalized, but perhaps a little childish for those interested in something more advanced.
  
• Samuel Adams Boston Brewery
  Visitors can tour the brewery to see how the beer is made, learn about the brewing process, and enjoy samples of seasonal and classic brews in the tasting room. It’s a fun stop for beer lovers and anyone curious about Boston’s brewing history.
  
• Taza Chocolate
  Taza Chocolate is a stone-ground chocolate factory in Somerville, just outside Boston, known for its bold, crunchy Mexican-style chocolate. Visitors can take a guided tour to see how the chocolate is made from bean to bar, explore the factory, and sample a variety of chocolate treats in the tasting room. It’s a must-visit for chocolate lovers looking for a hands-on, flavorful experience. Their chocolate is OU Kosher certified and pareve.
  
• Faneuil Hill
  Part of the historic area, it offers a glimpse into the city’s revolutionary past. Once a site for early colonial meetings and gatherings, it’s now surrounded by shops, restaurants, and historic landmarks. Visitors can enjoy walking tours, street performers, and the vibrant marketplace while taking in the history of Boston’s “Cradle of Liberty.”
  
• Newbury Street
  Newbury Street is Boston’s premier shopping and dining destination, stretching through the historic Back Bay neighborhood. Lined with high end and boutique shops, housed in brownstone buildings – it offers the perfect blend of modern with historic charm. A fun street to stroll down and enjoy the old and new of Boston.
  
• The New England Holocaust Memorial
  Holocaust memorial with 6 illuminated glass towers symbolically etched with 6 million numbers. It has personal quotes from survivors in a beautiful touching display.
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• Boston Public Library
  Besides being the first American Public Library, it is also a beautiful building with masterful murals and artwork all over and a beautiful garden. We stopped in on Shabbos to enjoy some A/C and were pleasantly surprised by the gem we hit upon.
  
• Pub Crawl
  Boston is home to a number of historical bars, some dating back to the revolutionary era. We did a sort of self guided pub crawl motzei shabbos to check out some of these spots. There are also established pub crawl guides that combine the freedom trail with some of these spots for a boozy history tour.
  Some of the historic bars include:
  • The Green Dragon Tavern
    Established: 1654 (original tavern demolished) – Known as the “Headquarters of the Revolution,” Boston patriots—including Paul Revere—plotted here.
  • Bell in Hand
    Established: 1795 – Often cited as America’s oldest continuously operating tavern. Served patriots and locals alike through centuries.
  • Beantown Pub
    While not historical itself, they pride themselves as being the only place you can drink a cold Samuel Adams while looking at the cold Samuel Adams – sincle they’re located right across the cemetery where he lays.
  • The Warren Tavern
    Established: 1780 – Frequented by Paul Revere and other Revolutionary figures; retains a colonial tavern feel.
  • Union Oyster House
    Established: 1826 – America’s oldest continuously operating restaurant; has a bar area frequented by politicians and authors over centuries.
  • Omni Parker Bar & Lounge
    Established: 1855 – the longest continuously operating hotel in the United States. It has hosted literary figures like Charles Dickens, served as the birthplace of the Boston Cream Pie, and is where JFK proposed to Jackie Bouvier.
  • The Black Rose
    Established: 1976 (Irish pub style) – Recreates an old-world Irish pub atmosphere; a local legend for Irish music and hearty fare.

Sunday evening we stayed the night in Hammonasset Beach State Park where we camped for the first time. It was a perfect end to a beautiful weekend. We hope to make it back to some of the items on the list above (or some new ones – we saw a holocaust museum is in the works) next time we need a quick getaway – maybe with the kids this time.

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avidtraveller

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