Out and about · Travel

New England road trip: Boston, Massachusetts

This post is the third in a series of blogs about our honeymoon trip to New England and New York City in October 2014. See all New England road trip posts.

The first stop on our New England road trip extravaganza was two nights in Boston, Massachusetts. Boston is a truly wonderful city – a mix of old and new that feels expansive but also very welcoming.

Day One: Cheesecake, the Top of the Hub and bowling
Day Two: Beacon Hill, Freedom Trail and Harvard
Day Three: Picking up the hire car and getting on the road

Day One: Cheesecake, Top of the Hub and Bowling

We were staying at the Hilton Back Bay hotel. Our room was large and comfortable, if a little generic but we had a nice view out across Boston. The hotel provided an excellent base for our day and a bit of exploring being conveniently located near the Prudential Centre.

Our first stop for some much needed sugar after a long flight from Heathrow and a taxi from Logan Airport was The Cheesecake Factory. Perfectly situated just around the corner from our hotel and recommended by friends, we popped in and assured the waiter we definitely wouldn’t be needing the food menu, thank you very much, just the one with the cheesecakes please. The list of available cheesecakes was IMMENSE and we were crippled by indecision. Eventually I chose Reese’s Peanut Butter Cup and was not disappointed. The cheesecake slices were delicious but so massive that even I couldn’t finish mine!

If you only do one thing in Boston, I would recommend having a drink at the Top of the Hub at the Prudential Centre. Encouraged by a positive review from a friend we decided to try it out and I’m really glad we did. We found our way to the Prudential Centre taking the lift up to the Top of the Hub and we were soon seated in comfortable window seats with the most perfect view across Boston.

We had a whole host of plans for our first day in Boston but cheesecake and a front row view over the city with a cocktail won out and I wouldn’t have done it any differently.

King's Bowling Alley, Back Bay, Boston
King’s Bowling Alley, Back Bay, Boston

We could have stayed there all night but bowling awaited! We read about Cheap Tuesday’s at the retro styled bowling alley, King’s. We turned up and booked into a lane, I bought us some Bud Lights, and we bowled the night away only stopping to have a quick moment of Taylor Swift appreciation with the girl on the lane next to us. I’d really recommend King’s for a fun evening – in addition to bowling they also have mutiple bars, a restaurant, skee ball, shuffleball and air hockey.

Our energy supply dwindling again we made our way to the Trader Joe’s around the corner to stock up on essentials (I just about resisted buying every Pumpkin-flavoured item in there) before collapsing for a comfortable night’s jet-lagged sleep.

Day Two: Beacon Hill, Freedom TRail and Harvard

The next day the serious business of Boston sightseeing began and we realised that we were in no way adequately prepared for our time in Boston. When you research the weather in New England in October, the websites advise that it could be snowing or it could be a heatwave. Basically, who knows? Being fans of all things knitwear we’d plumped for the former. Man, were we wrong! We arrived into a very, very warm Boston and soon realised our collection of nine jumpers each wouldn’t help us in the slightest.

We got the subway from our hotel to Boston Common where we spied a Peet’s coffee shop across the street. Undeterred by the odd fact that it seemed to be part of a bank (!) we each got the hot drink of our choice and something for breakfast (me a pumpkin scone, him an apple danish). We crossed back over to sit on a bench in Boston Common with a view of a fountain and the stunning Massachusetts State House. It was a perfect start to our first full day of our trip.

We soon got our first glimpse of some beautiful colours in the leaves whilst making our way across to Boston Public Garden to see the very sweet ‘Make Way for Ducklings‘ statue.

Next up on the day’s schedule was a walk around beautiful red brick Beacon Hill. If you ever find yourself in Boston make sure you have an amble around these incredibly picturesque streets with nice shops and café’s, lovely squares and houses you’ll fall in love with. We were only two streets in when we started working out how we could move there! The great thing about Beacon Hill in October is pumpkins. Lots of houses had wonderfully classy gourd displays and it seemed the classier the door, the smaller the pumpkin! Make sure to see Acorn Street – looking up the street from the bottom, the street is gorgeous and you’ll probably recognise it from a million Pinterest boards!

Realising it was lunch time we popped around the corner to the Cheers bar on Beacon Street. The pub, originally known as the Bull & Finch, was the origin inspiration for the setting of the TV show. We enjoyed stopping for a pint and some lunch – I had nachos and Nial had chilli which came in a mug (love the coloured tortilla chips) – and couldn’t resisting getting a tankard as a souvenir for Nial.

After refuelling at Cheers it was finally time to get going on the Freedom Trail. The Freedom Trail is a self-guided walking tour through Boston which highlights the city’s 16 main historical sites. Fascinating for history buffs as well as being a nice way to see the city, the Freedom Trail is a must do. Sadly we didn’t have time to complete the trail or go into all the places but we did see the Massachusetts State House, Park Street Church, Granary Burying Ground, King’s Chapel, Benjamin Franklin Statue, Old State House, Faneuil Hall, the Paul Revere house and Old North Church amongst others.

On our walk around we also came across David’s Tea and a new obsession was born. A lovely shop with helpful staff and a fantastic range of teas, I’m really gutted we don’t have David’s Tea in the UK. Nial bought me a couple of fancy fall-themed loose leaf tea tins (pumpkin chai! maple cheesecake!) as well as a cup with a raccoon and autumn leaves on it. Upon discovering we were on our honeymoon, the lovely assistant gave a voucher for a free drink to take into David’s Tea when we were in New York which was really nice of them.

After our time on the Freedom Trail, we made our way to Harvard University. Walking around the campus was a great experience, it must be a lovely place to study with open spaces and grand buildings. I couldn’t resist popping into one of the buildings and impressed myself by resisting the temptation to steal some education! We also visited the statue of John Harvard and sat in Harvard Yard for a while people watching and looking at the lovely colours on the trees and impressive buildings. Dragging ourselves away we went in search of food and found student-y bar Grendel’s Den in Cambridge which was perfect for quick pub grub.

With the night drawing to a close we headed back to our hotel to re-pack our bags and get our head around the plan for the following day. We had a wonderful time in Boston and we’d love to come back for longer but sadly the time had come to pick up our rental car and head out on the road.

Picking up the car and getting on the road

We had been dreading picking up our rental car for weeks prior to flying out to Boston. We’d read such terrible things online about Dollar who our travel agents had booked our rental with. On the whole the process went smoothly – we were obsessive about checking the detail on the agreement to make sure we weren’t getting charged for any extras we didn’t need and taking photos of existing damage to the car – with the only sticking point being that we didn’t really get long enough to accustom ourselves to the car itself before having to set out on the roads.

Having only driven small manual cars in the UK, our spacious Chevrolet Impala with its steering wheel on the wrong side and automatic gears mindboggled us for a while! I was first up to drive and it was quite stressful getting used to the Boston roads and driving on the wrong side whilst our sat nav adjusted to our new destination but once we were out of Boston and headed towards Salem, I was much happier and could relax.



See all New England road trip posts

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