Boston in the fall is a perfect destination to experience big city life – yet still enjoy nature at its best. Boston is a great city for two reasons: you can visit most tourist spots in a couple of days and it has great parks and walks that offer you the opportunity to learn about the early days of US history. It is also the perfect starting point of a road trip to Albany and the Niagara Falls.

I spent a day in Boston during my road trip around New England in the US – I flew into Logan Airport and rented a car for a week. For my first night I stayed at the Rodeway Inn at Logan Airport which was the cheapest option in Boston.

There was a special event in Boston that weekend so all hotels were fully booked! Even if there is no event, be prepared to pay higher prices for rooms in Boston as it is one of the most expensive places in the US.

Breakfast at Dunkin Donuts


I had a very early breakfast at Dunkin Donuts then headed into town to walk around the historic district. Once in the city the best thing to do is to find the waterfront and walk along towards Charlestown Bridge and join the Freedom Trail. The Freedom Trail will take you along all the historic sites that you need to see and the walk will take about 2-3 hours (Download it using THIS link).

I started my walk at the waterside where all the old bridges are. I really enjoyed looking at these fascinating historic structures as they tell a lot about the wealth of a city. The more bridges, the more money a city had to connect both sides of its river.

I joined the Freedom Trail at Charlestown Bridge near Langone Park. The walk takes about five minutes to Copp’s Hill Terrace and Charter Street.

Once you are on Charter Street it is the first right onto Salem Street to reach Old North Church. This church is a stop along the trail, behind which is the memorial monument to fallen US soldiers.

Boston Expressway Park

Boston Expressway Park

As you carry on, you will reach the Paul Revere Mall, a grassy park with several benches. Walk to the end and turn right onto Hanover Street, the main artery of Boston’s walking district. There are various restaurants and bars here if you are hungry or thirsty.

Historic Markets & the Holocaust Memorial

At the end of Hannover Street is a wide open space, which used to be the elevated Freeway through Boston. The freeway is now underground in a structure called “The Big Dig”. Thanks to the “Big Dig” it is super easy to get into town and parking is plentiful if you know where to look. It is also possible to park on the street, just make sure you don’t block the fire hydrant because that will be a fine of $100! Ouch!

The ugly roadway has now given way to a beautiful park full of flowers and fountains. A historic fruit and vegetable market is also here near the old freeway. The historic Haymarket Public Market sells everything from sea food, flowers and fruits and vegetables, so if you are peckish after the long walk you can fill up here.

Boston Cemetery

The Historic Boston Cemetery

Once you reach the end of Hanover Street, turn right onto the New England Holocaust Memorial Park. It is a sombre reminder of those killed in concentration camps across Europe.

The road from here will take you to Quincy Market, a historic market hall filled with restaurants and bars as well as shops. It is here where new and old meets in Boston. The high rises in the background contrast the historic Old State House, which stands looking almost lonely amid the forest of skyscrapers.

Walk up on Washington Street and turn right on School Street to reach the old cemetery and Boston Common. The cemetery is worth a wonder as it will remind you how old Boston really is.

Walk to Boston Common after the cemetery to admire the golden domed State Capitol and the park itself where Bostonians regularly enjoy a sunny day out!

Eating a Boston Cream Pie at the Omni Parker House Hotel

You cannot leave Boston without eating a famous Boston Cream Pie. The cream pie was invented by Omni Parker House Hotel on School Street and it is an institution to buy a cake and eat it in the cafe. The cream pie is quite expensive in my opinion, given it is a rather small slice – coming in at $9 a piece!