Things To Do In New England (Six Day Itinerary)

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New England, known mostly for it's rich colonial past, rugged Atlantic coast lines, beautiful mountain scenery throughout, out of this world fall foliage, and of course, the Patriots... is a fantastic and charming area of the United States that should not be overlooked.

New England is made up of six north Eastern states, however, this itinerary post will focus mainly on a road trip between Massachusetts and Maine.

We'll start off in Massachusetts, explore the city of Boston, and then head north to visit beautiful parts of Maine including the city of Portland and Arcadia National Park.


The itinerary finishes back in Boston, Massachusetts.

Of course, with so much beauty to see it's easy to wish we had more time.. but if six days is all you've got this itinerary will help you plan accordingly so that you get the most out of your trip to the beautiful northeast.



This itinerary briefly discusses Acadia National Park. For a detailed Acadia National Park itinerary  make sure to check out this post.

This post does not summarize everything that can be done, but features highlights of what we did on our own road trip - feel free to personalize it to fit your needs.


Arrive at Boston and explore city


museum of fine arts boston new england road trip


Day one is going to be a day of travel - use this day to arrive, get settled, and familiarize yourself with the surrounding area.

Our flight from Miami to Boston was rather short (only 3 hours and 20 minutes) and since there was no changing of time zones, we didn't feel jet lagged, which was great!

Visit the Museum of Fine Arts

Since we only had six days to explore we wanted to hit the ground running so as soon as we got settled into the hotel, we went off to explore the Museum of Fine Arts.

The MFA of Boston is the fifth largest museum in the United States, and includes hundreds of thousands of art collections. If you are an art lover, or simply want to explore a cool museum, this is a great easy thing to do on day one.


The Museum of Fine Arts offers free entrance on certain days and times of the week. Make sure to check out their calendar before your visit to see if you luck out!


image is from the MFA website - please check for updates.

Take a stroll through Back Bay Fens aka 'The Fens' 

If you're not into museums or rather spend some time outdoors, Back Bay Fens , also referred to as 'the fens' for short, is another great option.

This is a large greenspace or as google calls it, an urban wild parkland, that features multiple parks such as The Fenway Victory Gardens and a Rose Garden as well

In the fall, it is absolutely gorgeous with colors of oranges, yellow, and reds bursting all around. It is a large area, but since we were on bikes we were able to explore it quickly and easily.

Other things to do: Catch a sporting event. Boston is a great sports city and the home to many major league sports such as baseball, basketball, hockey and I'd count the patriots too.

where to stay in boston:


We like to be spontaneous and adventurous at times - and this was one of those times. We decided not to book our Boston hotel until we had arrived at Boston.

We do this often in big cities, that we are sure won't run out of lodging, to take advantage of last minute hotel deals. Obviously don't try this in small rural towns where you may be out of luck.

For this Boston trip we decided to gamble with our luck a bit and decided to use - a website that sells heavily discounted hotel rooms that go unbooked.



Of course the catch is that you don't get to see what hotel you are booking beforehand but based on our experiences in the past, it's always a great deal and we've always gotten awesome hotels each time.

This time was no different.

We lucked out with the beautiful and luxurious Hotel Commonwealth located on Kenmore Square - centrally located to many activities.

→ check prices now

how to get around Boston

what are blue bikes?

If you don't yet have a car on day one (we didn't rent ours until the 3rd day), but still want a faster way to get around, make sure to try Blue Bikes.

Blue bikes is a bike sharing program that is available in Boston (and other nearby cities). The way it works is - you find a bike hub near you, unlock the bike, and ride away.

You can return it to any nearby bike hub. Of course it isn't free - but it does provide a unique experience and a faster way to get around.

Uber and Lyft are also convenient and popular transportation methods to get around the city.



Fenway Park Tour

and Freedom Trail Self Walking Tour


Fenway Park Tour New England Road trip


Day two is going to be a full day, so put on those comfy walking shoes and get ready to explore some of Boston's most iconic areas.

Start your morning off early by scheduling a tour of Fenway Park - America's most beloved ballpark.

Even if you are not a Boston Red Sox fan, or a baseball fan in general, you can't pass up an opportunity to get inside and feel the rich history that this 100-plus-years-old park contains.


fenway park stadium tour new england road trip


It is the MLB's oldest park - and that alone is a good reason to come spend some time here...

The tour itself is fantastic, and not boring at all, even for people who barely know a thing about baseball (me).

You'll get to experience the park in a way that many others have not, and learn cool Red Sox facts that you'll later get to share with friends.


fenway park stadium tour new england road trip


Fun fact: Fenway Park features a roof top organic garden that provides fresh organic produce that is used in the parks' concession stands! How cool is that?


fenway park stadium tour new england road trip


After the tour maybe grab a quick bite to eat and get ready for the second half of this exciting day - it's time to walk the Freedom Trail.

how to walk the freedom trail in boston

The Freedom trail is 2.5 miles full of significant historical sites including but not limited to, museums, churches, meeting houses, burial grounds, parks and other historical markers that played a significant role in the American Revolution.It's one of Boston's most iconic features, and a must do if you're in town.

You can take part in one of the tours offered by The Freedom Trail Foundation, or you can do what we did and download the NPS Boston app that includes a self-walking audio tour of the Freedom Trail.


self walking tour freedom trail boston new england road trip


We did the entire freedom trail on foot, and even though it made for a long and exhausting day, it was still worth every step because it provided a unique way to explore and take in the beautiful city of Boston.

things to see on the freedom trail in boston:

Boston Common - America's oldest public park.

Granary Burying Grounds - Some of America's most notable citizens rest here (including John Hancock and Samuel Adams)

Faneuil Hall Marketplace - Once held America's first town meeting, now is a thriving marketplace with many stores and restaurants.

This is a great place to take a break from all of the walking, maybe grab a snack and get ready for the second half of the trail.

Paul Revere's House - Built around 1680 this is the oldest remaining structure in downtown Boston. If you're a history buff, you're going to want to experience this.

And finally Bunker Hill Monument - Try to take the stairs up (it's a work out!) but the views are spectacular, and once youre up there you can imagine being a patriot and having to look out and see for soldiers coming over the hill.


view of boston city on bunker hill

view from the top of Bunker Hill


Consider taking an uber or lyft back to your hotel so that you don't have to worry about the walk back... that's what we did.

If you have extra time check out these tours:



road trip begins towards portland, maine

Today your new England road trip officially begins so go pick up your rental, if you haven't already, and get ready to explore!



The main goal for today is to arrive to Portland Maine which is roughly three hours away from Boston. You can do with this day as you wish, as long as you are driving north towards your final destination.

Today is a great day to sneak in any last minute things or places you have not yet explored in downtown Boston or the surrounding area.

drive by Harvard University

We love college towns - so we knew we could not leave Boston and not at leasttt drive by Harvard. We also wanted to take a pic and send our parents a 'look mama we made it' text for the fun of it.

Harvard is a bit of a detour so keep that in mind.

learn about the Salem witch trials at Salem, massachusetts:

Our next must see stop was Salem, Massachusetts famously known for it's witch trials of 1692.

Salem is a great lunch stop and also a great place to get out of your car, stretch out your legs, and walk around the town a little bit before the rest of the drive up north.

Honestly, this visit was much more enlightening that I even realized it would be. It was surreal to learn the sad history of what occurred here in the 1600's and to visit the resting place of those who were victims of the killings.

There are several museums throughout the town but we only had time for one - The Salem Witch Museum.


have lunch at salem, massachusetts

Salem is a great place for a quick bite to eat. We found this awesome vegan gem called Organic Garden Cafe that had delicious raw vegan food. If you only try one item off the menu - make sure to taste the pizza (amazinggggg)!

By the time you reach Salem you are now only about 2 hours out from Portland. Feel free to make more stops as needed. We drove the rest of the way non stop to reach Portland, Maine as soon as possible.

where to stay in portland, maine:


The Old Port in Portland Maine is a historic district in which we stayed in on our one night in Portland. This quaint district features cobblestone streets and brick buildings which house many small boutiques, food stores and souvenir shops.

There is also a lively nightlife in this area that features pubs, breweries and cocktail bars if that's your sort of jam.

Plenty of hotels are also located here for your convenience.

We stayed at the Portland Harbor Hotel which was centrally located in the middle of all of the fun action. → check prices now



Head north to Acadia National Park 


If you're anything like me, a national park geek ... then you're going to be super excited for day 4, because we've FINALLY headed towards Acadia National Park. Yay!

But before that we're making a stop along the way.

quick stop at Fort Williams Park 

This park was such an awesome surprise for us. Fort Williams Park is a free seaside park that features a rocky shoreline, old military bunkers which make for awesome photography, large open playing fields with picnic tables, and of course an iconic lighthouse.

To say this park was picturesque is not enough.

And if you're lucky enough to visit in the fall, get ready for spectacular hues of oranges, reds, and yellows.


new england road trip

how to get from portland maine to bar harbor maine (acadia national park):

The rest of the drive from Portland to the entrance of Acadia National Park is around 3-4 hours depending which route you take. The map above shows the quicker inner-land route but if you've got an extra hour and want to take in the beautiful views of small quaint coastal towns, then perhaps sticking to US1 North through Camden is your best bet.

It's a nice and easy drive through the highway that rides along the coast and through beautiful small coastal towns. The drive itself is an adventure, and if you visit in the fall you will enjoy watching hues of oranges, yellows, and reds through your car window as you drive by the foliage.


where to stay in bar harbor, maine:

There is no lodging located within Acadia National Park (with the exception of a few campgrounds) so we decided to stay in Bar Harbor, Maine which is located just five minutes away from the Park Loop Road (Hulls Cove Visitor Center) entrance station.

Bar Harbor is a small town located on Mount Desert Island. Surrounded by the enchanting cliffs and mountains of nearby Acadia National Park, it is a gorgeous setting to unwind at after busy days of hiking at the park.

We stayed at Bar Harbor Inn and Spa and recommend it 10/10. It was comfortable, 5 minutes away from the park, easy parking, great customer service, and the view out of the balcony window was unreal.

→ check prices now


Where to eat in bar harbor, maine:

For food we mostly stayed away from the many restaurants in downtown and instead opted for healthier alternatives at A&B Naturals. We had breakfast and dinner here a few times during our stay. They have a small cafe counter as well that has a few fresh options like juices and smoothies - a ton of organic, vegan and vegetarian options available.



Full day at Acadia National Park


Finally, there is no driving today. Use up this day to enjoy the national park. You can do as much, or as little, as you prefer to do. We wanted to take advantage of the entire day so we woke up early, got some breakfast at A&B Naturals, and hit the road to the trails.

For a detailed Acadia National Park itinerary and for specific things on what to do at this national park see this post.


Acadia NP in the morning

departure in the evening



This day will vary depending on what time your departure is and how and where you are departing from.

We had to be back at the Boston airport in the afternoon and from Acadia NP to Boston airport is 5 hours. Make sure to plan accordingly.

We were able to snag a late afternoon flight back home which gave us some extra time in the morning. After checking out of the hotel we went back to acadia np for a few hours before making the long (but beautiful) drive back to Boston International Airport.

Have a safe flight home and hoped you enjoyed your weekend in beautiful New England!!



Want to see more travel related articles?

Check out this article to learn how to spend 24 hours in Seattle.


with love + gratitude,

Jen ♥


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About Jen

A former registered nurse turned stay-at-home-mama, yoga teacher, and holistic health + wellness enthusiast. I share my homemade healthy recipes + natural living content to help women and moms live healthier and happier lives.

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