Trees strung with colorful lights all over the Boston Common, Bostonians huddled in pubs drinking to the season, the smell of warm babkas at Bakey in Quincy Market….December is a wonderful time to enjoy a visit to Boston. It is cold. I am from New York and have been through a blizzard or two but still found the cold in Boston (when it gets below freezing and the wind blows) more than a bit chilling. Not that Bostonians seem to mind, as most of them are still walking around in sweatshirts and hoodies, which is something to see in itself!
I had a wonderful time during our recent four day visit a week before the Christmas holiday…here is some of what we did:
Beacon Hill
Beacon Hill is one of Boston’s most picturesque neighborhoods, especially during the holiday season. Streetlights illuminate the historic brownstones adorned with festive wreaths and garlands, creating a charming holiday atmosphere.
Along Charles Street you will find unique boutiques like Upstairs and Downstairs, a home goods store with art work as well, and cozy cafes like Tatte Bakery and Beacon Hill Books & Cafe. – I loved the glimpse of white table cloth covered cafe tables and Bostonians huddled inside against the cold in the beautiful cafe. We only had time to head upstairs to the bookstore, where I picked up a book, something I like to do on every trip.
The bookstore is decorated like the living room of a well-to-do owner of one of the neighboring brownstones, so charming and welcoming. I could imagine I was in the living room of Olive Chancellor in Henry James’ novel “The Bostonians”, albeit the 2025 version!
We got a late lunch at The Paramount, a diner and mainstay at this location since 1937 serving American comfort food for brunch and beyond. Afterwards it was a short two block walk to iconic Acorn street. Acorn street was built in the 1820s as a service lane, and the uneven, rounded cobblestoned street is likely original.
Along with the historic brownstones that line this street, it offers a unique glimpse into what 19th center Boston may have looked like and is said to be the most photographed street in Boston. One of the advantages to visiting in winter is the usual crowd of tourists were absent and I was able to get a snapshot of the street itself.
In the evening we went to two of our favorite establishments in Beacon Hill, Cheers and 75 Chestnut. Cheers on Beacon street is a popular tourist stop, and since we used to watch the show we couldn’t resist going into the gift shop, looking at the props and snapping a picture by the “Cheers” sign outside.
However, a visit to the Bull and Finch pub downstairs (which is said to have inspired the “Cheers” TV series) was the most fun. It had that comfortable, local and lively pub vibe that you hope to find when you come to visit a city like Boston. We settled next to the bar with two Samual Adams brews and just enjoyed the scene.
Then we headed out for dinner at the neighborhood favorite 75 Chestnut. Set in a charming brownstone with flowering window boxes outside, this restaurant serves upscale American food at moderate prices. You will usually see it filled with locals, and the host circles the room making sure everyone is happy. I enjoyed their seared Atlantic cod in an apple cider butter sauce over black lentils. The almond cake with cinnamon ice cream with caramelized apples was yummy and perfect for the season.
Afterwards we walked through the Boston Common towards our hotel. In the subzero temperatures, our drinks kept us warm, and the holiday lights sparkled bright.
I was taken in by this neighborhood’s timeless beauty and holiday spirit.
Downtown and Back Bay
Downtown Boston is a vibrant area that bustles with shoppers, business people, and tourists. With the Boston Common and State House nearby, it is a blend of towering skyscrapers and historic buildings. The hotel we stayed at, the Hyatt Regency, located at Downtown Crossings, meant we were centrally located to much of Boston. Our hotel seemed to cater to mostly business people throughout the week (it seemed like every day we saw the pilots and cabin crew of Lufthansa hanging out in the lobby!), but it was a comfortable stay for us with all the expected amenities including a flavored water kiosk which we used on a daily basis. We were sad we didn’t get a chance to try the sizable pool and sauna in the hotel’s gym. No time –
The hotel had a restaurant, Avenue One, but we decided to explore two other breakfast options nearby: Cafe Bonjour where we shared a scrambled egg platter and French toast with berries. You can see their pride in the fresh and organic produce they use. I honestly couldn’t think of the last time I’d had French toast made that well. We loved the French bistro atmosphere too. For a quicker meal George Howell Coffee was a great option, where we devoured delicious egg, sausage and cheese breakfast sausages in a rather crowded cafe with a trendy vibe. A few customers next to us were on conference calls but that probably doesn’t happen on the weekends.
For shopping, there is plenty to do. Go through the shops and Macy’s department store, or browse the used books in Brattle Bookshop on West street. Brattle Bookshop was established in 1825 and is one of the nation’s oldest used bookstores. It has three floors including one devoted to antiquarian books, but you can also get a book for $5 or ask for help to get used books to decorate your home with.
A walk through the Boston Common (America’s oldest public park, opened in 1634)
will bring you to Copley Square and the Back Bay neighborhood. If you haven’t finished with shopping, then head over to the Prudential Center, a 52 floor mall with shops, eateries and a rooftop bar, restaurant and observation deck. Tickets to the observatory deck were around $40 per person, we opted not to go this time and headed back to Copley Square.
In Copley Square, famously the finish line on Boylston street of the annual Boston Marathon, you will find Trinity Church and The Boston Public Library, both of which we toured and are well worth a visit.
We caught the 11:00am tour of Trinity Church which was led by one of its rectors. An amazing one hour tour, our small group learned so much about the history of the church which is one of the nation’s top architectural sites and a landmark building. I loved the many stained glass windows, especially the one of Christ in a blue background located at the back of the church behind the organ. It is said to have been placed there to inspire the minister when he gave sermons.
The Boston Public Library is beautiful , consisting of an older building with a grand marble entryway,
Bates Hall which is the reading room known for its grand barrel-vaulted ceiling, green lamps and scholarly atmosphere,
and the Abbey room with a 15 panel mural painting of the Holy Grail story done by Edwin Austin Abbey.
We took a self-guided audio tour of the library, then rested in the spacious cafe located in the modern wing of the library where you can check out books.
During our tour of Trinity Church we learned that the landmass in this area was originally much narrower…as Boston developed from colonial times they moved ground from the surrounding hills and used it to fill in this marshy area to provide space for more residential housing. The area is now called Back Bay. It has two notable streets, Newbury Street which has higher end stores and some good seafood restaurants like Atlantic Fish Co. and Saltie Girl (this time we opted for some juicy burgers for lunch at Capital Burger), and Commonwealth Avenue which lights up with Christmas lights at night.
There’s a constant energy here, with locals and visitors alike enjoying the mix of culture, commerce, and history that defines the heart of Boston.
Holiday Markets and Concerts
Snowport
The Christmas market at Seaport is called “Snowport” and was a lot of fun to visit. We went there during a Monday afternoon, so we didn’t encounter large crowds. It was a fairly easy 20 minute walk from our hotel, just across the bridge on Seaport Avenue and into the Seaport district, which also has some shopping. Since it was super cold that day, we hustled into the market and made a beeline to the Baked Cheese Hause for some yummy cheese raclette sandwiches, which we washed down with some outstanding Gluehwein in the outdoor drinking tent under some heat lamps.
There were a few more food options…we tried the savory ham, cheese and figs crepes (yum) then grabbed another Gluhwein and browsed the neighboring wooden stalls full of crafts and seasonal gifts.
SoWa Holiday Market
The other holiday market we visited was the SoWa Holiday Market, located in the South Boston neighborhood. We took an Uber there and since it was raining that evening it worked out well that this is an indoor market. There’s a $10 admissions fee which you pay at the door.
Aside from the many stalls with clothing, books etc. What we enjoyed the most was the hot chocolate with a toasted marshmallow ring around the rim….most people seemed to be walking around with one of those and we could see why…it was an amazingly good hot chocolate!
That was we all consumed because we had dinner reservations at nearby Myers + Chang. Dinner was the absolute best, we met the chef and co-owner Joann Chang who was bustling about greeting diners and taking them to their tables. The food was phenomenal, I still think about the salty-sweet black bean Udon noodles with chicken I had and wish I could have it back home!
Boston Pops Holiday Concert
One of the highlights of our trip was attending the Boston Holiday Pops concert, put on by the Boston Symphony Orchestra (we purchased tickets online in advance). We were surrounded by mostly Bostonians it seemed, and many were dressed up in glittering dresses and their holiday best, something I miss seeing in New York where people seem to have stopped dressing up to go out.
There was an air of childlike innocence in their celebration of the holiday spirit, as the orchestra played some well-known holiday tunes like ”Winter Wonderland”, and an actor narrated the story “A Christmas Carol” by Charles Dickens to background music played by the orchestra.
Santa came to greet the audience, and in the end everyone joined in to sing Christmas carols along with the choir. It was a jolly good time and definitely puts everyone in a holiday mood!
Harvard University in Cambridge, MA
We took the subway, called the “T” to Harvard University in Cambridge, a few stops away across the Charles river. It was super easy to take the “T”, you can get one way tickets at the ticket machines at the entrance and they even have attendants there to help you if you need.
Once we got off the train at Harvard Square (a historic gathering place since 1640), we made our way to the building that used to be the Radcliffe women’s college and is now the Radcliffe Institute for Advanced Study where the Harvard Visitor’s Center is located.
We didn’t just get a map for our self-guided tour, the attendant there spent a lot of time explaining all the points of interest to us and answering our questions. It became clear we could easily spend the entire day here, but since we had allocated just that morning to our visit, we decided to see Harvard Yard and the Harvard Art Museum.
Inside the iron gates leading to Harvard Yard you will find Widener Library (note it is open only to students), the statue of John Harvard,
and the Harvard Memorial Church, which has served the Harvard Community for over four centuries.
Inside you could feel the weight of all those years of gatherings, ceremonies and events that had occurred and there is a grand air of solemnity in the church.
The Harvard Art Museums (three museums housed in one beautifully designed building), hold an impressive collection of art that reminded me of a smaller version of the Metropolitan Museum of Art in New York. It is free to the public, and after checking in our bags (also free), we made our way through many collections from all over the world, including American art and masterpieces of European art from artists like Matisse, Van Gogh, Monet and Seurat.
I was drawn specifically to the Budhist statues in the Asia section.
Faneuil Hall, Quincy Market and the North End
There is so much American Revolutionary history in Boston, and the city does a great job bringing you all the points of interest in a path called “The Freedom Trail”, a two and a half mile path paved in a line of brick that begins at the Visitor’s Center in the Boston Common and ends at the monument on Bunker Hill commemorating the revolutionary battle that was fought there.
See my post on the The Freedom Trail – Boston, MA for more.
Faneuil Hall and Quincy Market
The trail leads straight through Faneiul Hall, Quincy Market and the North End neighborhood. Fanieul Hall is one of my favorite sites along the Freedom Trail. The visitor’s center and military museum are free to the public. This was the location where colonist used to gather to discuss events, hold ceremonies and more. The Articles of Confederation were read to Bostonians for the first time from the balcony of this building. It is where the Boston Tea Party began. A visit here will truly take you back into time.
Located in front of the building is a plaque that marks the location of the Boston Massacre, which is said to have sparked the American Revolution.
Next to the hall is Quincy Marketplace, which is full of food vendors of all kinds, souvenir shops and brand name shops including in the South market and adjacent mall.
I got a Boston knit hat as a souvenir, and since it was morning I splurged on a warm and flaky raspberry Babka from Bakey. If you haven’t gotten your lobster roll yet, you have one more chance to get one here!
The North End
That evening we walked up to the North End neighborhood for dinner. This is Boston’s oldest residential area, dating from the 1630, and includes the house of Paul Revere. Home to waves of immigrants it eventually settled as “Little Italy” and today is a center for Italian food and pastry in Boston.
We had reservations at Ristorante Lucia, but were a little early so we walked up and down Hanover street. We happened across St. Leonard Church, a catholic church that had an open door so we went inside for a while for some peaceful (and warm) meditation.
It was in plenty of use that evening as locals went in and out, offering up prayer and also sitting in solemn thought in the pews. There was a beautiful Nativity scene out front that reminded us what the season is really all about.
After dinner, a highlight of the evening was the luscious and flaky cannoli that we got at Mike’s Pastry, serving Boston for over seventy years and undoubtedly the best cannoli in Boston!
I recommend getting the pistachio, chocolate dipped, and the strawberry.
Then we walked back to our hotel, not minding the cold at all (kinda like a Bostonian), our hearts full of warmth and good spirits.
What we witnessed during our visit aside from the festive lights, good food and monumental history was the spirit of the people. They truly embody their motto “Boston Strong”. Everywhere we found friendly, good people and we enjoyed the city comfortably in a low stress environment. in the hustle and bustle of the season that may have been the best gift of our getaway to Boston during the holidays in the end.
Date of trip: December 2025
The Full Itinerary 