An Epic New England Road Trip – Places You Need to Know

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Memorial Day Weekend 2014 saw us venture on a pretty spectacular yet hectic road trip around the New England states and across the border into Canada. Road tripping from Boston to Canada and back in just four days really tested our organizational skills as we still wanted to see as much as possible during a short timeframe. When you think about amazing road trips…well there are not many that we have experienced so far that come close to the beauty and experiences we had on our epic New England Road Trip!

Rather than trying to cram all of what we did into one post, this will give you a brief overview of what we did on the way to Canada and later we will release part two that shows our route back from Canada to Boston.

We LOVE road trips! One of the great benefits of living in the States is that you are able to experience so many of them. If you are looking for some alternative options, check out this post on other amazing US road trip itineraries that features a similar New England road trip but from Montreal to NYC.

The Route

new england road trip

Flying out of Memphis on Wednesday evening, connecting in Baltimore and arriving in Boston just before Midnight caused our first issue – where to sleep the first night?

Hotels close to Logan International Airport in Boston are not cheap, plus you have to consider how you will get to the hotel. We considered staying overnight in the airport terminal and had it not been for a long drive ahead the next morning, I’m sure we would have chose this option.

Fortunately we found a pretty good deal on a Holiday Inn Express that offered a free airport shuttle for $165 per night which is still pricey for only 6-7 hours but at least we had a good night’s sleep!

Here are the US states and Canadian provinces that we visited during this road trip to Canada:

New Hampshire

Driving north from Boston Airport in our Chevrolet Cruze saw us cross the state line from Massachusetts into New Hampshire. I have to admit that our time in NH was pretty uneventful as our initial plan was to venture west to Manchester, NH but we decided instead to go directly north heading towards Portland, england road trip

We did wander off the so-called beaten path rather than staying solely on the interstate and stopped in the quaint harbor town of Portsmouth though aside from a Memorial Bridge and a few shops, there wasn’t much activity on a Thursday morning.


After breezing through state of New Hampshire, we crossed into Maine where we spent much of Thursday driving north to the Canadian border.

ogunquit new england road trip

Entering into Maine we again headed off the interstate, this time for a quick coffee break in the charming town of Ogunquit.

We decided to spend some time in Portland primarily to visit the Portland Head Light. This lighthouse is a perfect spot to walk around and take in some scenic views of the Eastern coastline overlooking the Atlantic Ocean. When we first arrived, the lighthouse was partially covered in mist and visibility over the ocean was short but even in the short time we were there, it was pretty cool to see the mist rise and everything in the landscape become more prominent.


Maine is one of the more picturesque states to drive through and the further north you go, the more scenery you find with a variety of great spots along the way to just pull over on the side of the road and take some memorable shots.

Quebec City

Crossing the Canadian border in Maine was a painless process and we were soon back on the road though immediately we found ourselves feeling like we were in the heart of France. Every sign and direction was in French and this was when I appreciated those long French classes I had taken during my high school years.

The drive from the border to Quebec City takes about 2 hours but you pass through several villages that give you a brief insight into what Quebec City is really like. Arriving late Thursday evening, we checked into our hotel and then had dinner at Le Cochon Dingue.


Our time in Quebec City on Friday was spent exploring Montmorency Falls and Vieux Quebec which are certainly two of the more popular attractions here. We certainly appreciated our time here though our time was cut short given we headed to Montreal that evening.


The drive from Quebec City to Montreal can be taken either north or south of the St. Lawrence River. We opted for the northern option given that it passed through Troix Rivieres which we expected to have a little more to see than it really did. This route to Montreal took about 2 1/2 hours, again a little longer than anticipated but a scenic enough drive to make it interesting.


We spent Saturday morning exploring the Olympic Stadium before heading downtown to Old Montreal. Montreal was probably our most disappointing location throughout this whole trip but I don’t think it helped that there was so much construction taking place downtown that really spoiled the aesthetic appearance of the city.


The first half of our Memorial Day Weekend road trip saw us venture through three US states and across the border into Canada taking in both Quebec City and Montreal.

I would certainly say that the highlight of our trip was the time we spent in Quebec City and we are both eager to head back there again to explore further. The relaxing feel of the city and the nature of the ‘Quebecoise’ locals makes this a really attractive city to wander around.

Have you visited the New England states in USA? What about crossing the border into Canada?

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Chris Boothman
Chris Boothman is the co-founder of A Brit and A Southerner. Born near Manchester, England, Chris moved to USA in 2006 where he soon after met his wife and travel partner in crime, Heather. They have since embarked on an amazing journey of travel as they challenge others to follow in their paths of working full-time but also being able to travel frequently! If you have any questions or comments, please feel free to contact Chris at [email protected]


  1. That sounds like a lot of driving, but it sounds like the distances covered were also do-able. So nice to be able to see different things in such a short timeframe. Unlike where I live, I have to fly a long distance just to get to a destination.

    • Noel, it was quite a bit of driving for sure, I am not going to lie! But this is such a gorgeous part of the USA that it was very scenic and as you can see we broke up the trip into various stages, just as we did in the second half of the trip on our return from Canada. We saw everything that we wanted to during the four day trip but of course in an ideal situation you would have longer to explore each location more.

    • Cheers Lorrie, it really was an exciting trip and I am sure you will love the second half just as much on our return from Canada to Boston! That post will be available next week before we start going into more specific details on our experiences at various attractions along the route.

  2. I’ve always wanted to go to Maine and eat all of the lobster. This road trip looks amazing! I’ve crossed the Canadian border a few times, mainly to Toronto. I really like it there. I’m hoping to go back and visit Vancouver and Montreal soon.

  3. Looks like you had a fabulous time. I just love Quebec and would love to go back. Long weekend road trips are the best, aren’t they? Except when you realize that you need one more day to catch up on sleep before returning to work. I am definitely having that problem this week from my long weekend. I can’t wait to read the more detailed posts. I haven’t explore much of the New England states and want to see what you have to say about them 🙂

  4. I am jealous of your road trip. As a Boston native, these are some of my favorite locations! Ogunquit is the beach town that my family goes to every summer! Such beautiful beaches and beautiful charm in the town (before the crowds set in!). Portland is one of my favorite places in Maine (which is hard because I love the whole state). They have been going through a food revolution in the last few years so next time you are in town stop at one of the fantastic restaurants! I love Portland Head Lighthouse though, I was just there in November – beautiful views! Glad you enjoyed your drive!

  5. I love your new header!

    This is one of my dream road trips. I love this area of the US and Canada and hope to do something similar some day, even if I only have a long weekend in which to do it.

    • Thank you so much for the feedback on our new header, we really appreciate that and glad that it didn’t go unnoticed! I hope you get to venture to this part of the country because it really is stunning. Of course we would have loved to spend more time there but as with many of our trips we had to be realistic and saw as much as feasibly possible.

  6. Looks like a fun road trip! I road tripped with my family once from Seattle to Banff, the scenery was beautiful! The east side looks really pretty as well

    • The North East part of USA really is a gorgeous part of the country Samantha. All six states are unique but have gorgeous landscapes and there are picture perfect opportunities all over the place. I bet that drive from Seattle to Banff was awesome though, we would love to do that!

  7. Oh no I’m so sad that Montreal was disappointing for you! Although I can understand the construction being a pain…don’t you know we only have 2 seasons in Canada? Winter and Construction 😉 seriously though you will have to come back sometime and give it another chance, it is a great city!

    • We definitely plan on giving Montreal another shot! Old Montreal looked really cool, in many ways similar to Old Quebec so that definitely looks like it would be worth exploring. Of course the construction spoiled it a little but we will certainly head back there 🙂

  8. I’m impressed that you fit all that in a 4 day trip! Looks like a great weekend. I love the picture of the lighthouse in Portland and can’t wait to hear more about your time in Maine! That’s one area of the US I have been dying to see, although I think I’d have to stop and fill myself up with lobster 🙂 The lighthouse really does look breathtaking!

  9. Wow you guys must love to drive. You did manage to hit great spots along the way. Some of my favorites! Next time your in Boston, make sure to let me know. I’d love to show you some of my favorite sites and have a cup of coffee! Looking forward to seeing what you discovered here.

    • We will definitely let you know the next time we head there Alison! We had a great time and we have so much material to write about from the trip, we wanted to start with a couple of overview posts but will go into more specific details over the next few weeks. LOL, I’m not sure if its so much that we love to drive rather we just love to explore as much as possible during a short timeframe which kind of forces you into driving from point A to point B.

    • Great choice and of course you have to visit the lighthouse there! The downtown district is also pretty cool though we spend much time there to do it justice.

  10. So glad that you enjoyed your trip! As I posted in the FB group my husband and I took our *winter* honeymoon to Quebec City. We had such a blast. It’s so funny even just walking around and dining took up so much of our days. We loved it, so beautiful. We also went dog sledding. Awesome, yet terrifying. We also ate at Le Cochon Dingue for lunch one day I believe and thought it was tasty and fun. 🙂 My FB post for this week was our short 24 hours or so in Boston after our Maritime Canada cruise. We really enjoyed that as well. I am sure you will be reading about it soon if you haven’t already. 🙂 We have not yet been to Montreal, though I think it would be fun to see the more urban side of Quebec. I would love to go back to Quebec City really! Over and over. 🙂 Never been to New Hampshire or Maine… But Maine is high on my list! Will have to check out this little town when we go someday! 🙂 -Alexandra

    Simply Alexandra: My Favorite Things

  11. I’m am glad you made your way to Canada! Quebec City is amazing, isn’t it? Loved the picture you took around Olympic Stadium in Montreal. The blue skies made the picture all the more beautiful and reminded me of one of the reasons why I love Canada, the ‘homeland’!! I don’t know if you have ever been to Alberta but Calgary to Banff and then on to Jasper makes for one amazing road trip through the Rockies!!

  12. Wow you certainly had an epic weekend! Quebec City has been on my mind a bit lately. I’ll be heading to Canada next year and was thinking of just visiting the west but my mind is slowly swaying towards the east as well. It looks stunning and I’d been keen to read more about what you got up to there.

  13. Wow…. that is quite a lot of drive…. Next time you in Boston let me know… I would love to take you to my fav places… I am heading to Canada soon from Boston next week… Can’t wait 🙂

  14. Did you have to get currency exchange before hand or was American money ok to use? me and my best friends going on our first road trip were excited but so many questions.


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