Three Days in Boston during FallIf you asked me before I started my East Coast Fall Road Trip what city I was most looking forward to visiting I would have definitely answered New York. Poor old Boston wouldn’t have even been considered. Despite knowing it was one of the oldest cities in the US which would usually appeal massively to the history lover in me, I just didn’t think Boston would be any competition to New York.

Turns out that I couldn’t have been more wrong. Boston is now one of my favourite cities in the United States, and I am so glad that I got to experience fall in Boston.

In fact, Massachusetts was my favorite state on the East Coast, and I wrote a seperate piece about all the small towns in Massachusetts I loved as much as Boston.

Checking out the Boston historic buildings during fall in Boston

We only spent three nights in Boston so we barely scratched the surface of what the city has to offer but we absolutely loved what we did get a chance to experience. It was overcast and raining for much of the time we were there  – damn fall weather – but I loved it anyway.

Now that has got to be real love.

There is just so much to do in Boston and this post highlights a lot of the activities on offer.

But for us, there wasn’t one thing in particular that made our time in Boston during fall so enjoyable but rather a coming together of a lot of different things:

Our Boston Accommodation

We splurged and booked a private double room at the new Chinatown HI Hostel which was walking distance to pretty much everything we wanted to see. The room was very spacious, modern and the bathroom was nicer than most hotel bathrooms that I have experienced. The hostel had all the amenities of a great hotel while still having the fun energy of a hostel. It wasn’t cheap but for convenience and luxury it was spot on and made our stay in Boston that much better.

The Food in Boston

Oh the food! Boston is well-known for its fabulous food scene and rightly so. From incredible Pho in Chinatown to pizza by the slice in the city, we didn’t have a bad meal during our time there. I’m kicking myself now for not trying two of Boston’s iconic dishes: Boston cream pie and Boston baked beans, but I did have clam chowder under the beautiful dome of Quincy Market and it was fantastic. I followed up the chowder with a creamy scallop pie then had to go back to the hostel for a nap to sleep off my food coma (totally worth it).

Pizza in Boston - the perfect meal during fall in BostonVisiting Quincy Market for lunch during fall in Boston

Because it was fall in Boston when we were there, I overindulged in Pumpkin Spice Lattes (no regrets) as well as Samuel Adams beer at the English style pubs tucked away around the city. Much to our delight, Boston has the most English pubs I have seen anywhere outside of the UK and the UK does pubs better than anywhere else in my opinion.

Pumpkin Spice Latte during fall in Boston

When we visited nearby Cambridge, I enjoyed wandering Harvard where there was some beautiful fall foliage, but my highlight was eating at the burger joint Mr Bartley’s down the road, with its outlandish burger names and buzzing atmosphere. I ordered the ‘Skip Gates’ burger, a behemoth of teriyaki chicken, grilled pineapple and boursin cheese served with onion rings, and washed down with the best homemade lemonade. Perfection.

Boston Bar during fall in Boston

After seeing it on ‘Man v Food’, we had to go to the Barking Crab Restaurant. It may be touristy but as we were tourists in the city we embraced it and stuffed ourselves with Dungeness crab legs, peel and eat shrimp, and sweet potato wedges while listening to live music.

I didn’t get a chance to try out any of the food trucks that operate around Boston, and there are a lot, just one of the many reasons I need to get back there!

Boston’s History

Quincy Market, Boston in fall

Founded in 1630 by Puritan settlers from England, Boston’s historic past is tangible in its preserved historic buildings. Unsurprisingly it has a very English feel to it and after six years living in London, it made me feel right at home.

Wandering the neighborhoods of Boston in fallDowntown Cambridge Massachusetts - an easy half day trip from Boston in fall

Boston was the scene of several key events during the American Revolution with the most well-known being the Boston Tea party, where a shipload of tea was ruined by political protestors who dumped it in the harbour to protest the Tea Act.

We spent a morning walking the Freedom Trail which is a self-guided walk that takes visitors between historically significant points around the city.

One of my favourite spots on the Freedom trail was the Granary Burial Ground on the edge of Boston Common, where Benjamin Franklin’s family and Paul Revere are buried. A lot of the hand-carved stone gravestones are detailed with winged skulls and are dated back to founding of the burial ground in 1660.

Granary Burial Ground during fall in Boston

The trail continued through the Financial District past Faneuil Hall and Quincy Market to the Italian North End where Paul Revere lived (his house is still standing) and on to the expansive Copp’s Hill Burial Ground. The last stops were over the bridge in Charlestown where we joined a free Ranger led tour up to Bunker Hill to learn about the Battle that took place in 1775 between the Americans and the English during the Revolutionary War.

Visiting Paul Revere's house during a fall trip to BostonCopp's Hill Burial Ground during fall in Boston

Back in the city we walked the cobbled streets of affluent Beacon Hill. It is a leafy suburb with regal terraced apartments and exclusive English pubs. Old fashioned gas lamps switched on as night set in and with the rain-slicked streets it made me think of London, but an idealised version from the turn of the twentieth century.

Beacon Hill during fall in Boston

The Great Outdoors in Boston

The most iconic green space in the city is the centrally located Boston Common. The Common is the oldest city park in the USA and encompasses a sprawling 50 acres of land that includes walking paths, a duck pond, memorial statues, a bandstand and baseball fields. I loved these cute duckling statues following their mother.

Boston Common ducklings during fall in Boston

We had really wanted to hire bikes and bike the riverside path to Harvard University in nearby Cambridge but with the weather being so rubbish, we took the subway out there instead. Once there we walked around the wooded grounds and saw some students with a pet baby squirrel that was running over their shoulders. With the fall foliage and with the background of handsome stone buildings it was quite beautiful.

Harvard University during fall

Another great spot for a wander was the harbour walking path. On a foggy morning everything was still and we felt like the only people in the world as we walked past wharf buildings and boats docked in the harbour. I have always found fog to have a mysterious quality that I love and it gave the setting an ethereal quality. The fog was thick when we walked over the Fort Point Channel bridge one evening, with the city lit up and hazy through the soupy mist.

Boston Common during fall in Boston

The Vibrancy in Boston

Vibrancy and history don’t often go hand in hand but I think that Boston is an exception to that rule. In contrast to the genteel historic streets of Beacon Hill was the edgier neighbourhood of South End Boston. Although there are lots of beautiful Victorian row houses, there is also a vibrancy born of the young urbanites that call the South End home, and this is reflected in the funky stores, eclectic eateries, art spaces and street art. We also saw street art scattered throughout other parts of the city with the imposing ‘Giant of Boston’ standing out as my favourite.

The Boston Giant - some of the street art in Boston

I rarely enjoy shopping but when I needed to replace my boots we set out for Newbury Street in the suburb of Back Bay. I loved the big brownstone houses and trees wrapped in fairy lights. People flitted between the big name shops that are interspersed with smaller design boutiques, restaurants and bars. Despite it being three weeks before Halloween, there were decorations in shop windows and jack-o-lanterns on front stoops which lent a festive air to the area.

Halloween in Boston - one the fall in Boston highlights

Along with Boston’s numerous historic buildings, tons of eating options, great shopping and accessible harbour, I think it was the feel of the city that really captured me. It is such an exciting mix of the old and the new and a city that I will definitely return to.

And you should definitely visit Boston in fall.

Have you been to Boston? What was your favorite thing about the city? Have you experienced Boston in fall?

2 Comments on How to Spend Three Days in Boston During Fall

  1. I love Boston! I lived there for a few months during college but haven’t been back in at least 5 years! I’m sure things are different now but your pictures are bringing back all the best memories 🙂

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