This summer we took a road trip to a foreign city new to my family- Montreal, Canada. Driving from Boston to Montreal is an ideal New England road trip. In a pretty easy half-day drive you can be in not only a different country, but one that feels foreign. Montrealers speak French, along with English, and the city has a definite European feel.

Our home base is Providence, Rhode Island, so I was actually traveling from Providence to Montreal, but for the sake of my readers, I will use Boston as a starting point.  We drove through Boston on our way out. It is fairly equidistant to travel through New Hampshire or Vermont to get to Montreal from Providence or Boston, so we chose to travel a different route for each leg of our journey. This gave us a chance to explore more of our beloved New Hampshire, but also one of my favorite states, Vermont. Either route takes a little under 5 hours.

Road trip from Boston to Montreal

Stops for your Road Trip from Boston to Montreal Through New Hampshire

Lincoln, New Hampshire

We left for our adventure after a workday, so didn’t want to do the whole trip in one day. We stopped in one of our favorite New Hampshire towns for the night, Lincoln. Read all about why we love Lincoln.

Stop to See the Longest Candy Counter in the World!

Chutters in Littleton, New Hampshire claims this superlative! There is enough candy here to make the rest of your drive sweet and this is a cute town to see.

How to Visit the Derby Line on your Road Trip

On my first trip up this stretch of road I kept seeing signs for Derby Line that intrigued me. After we got to Montreal I did some research to find out what this line is. The Derby Line is the estimated line half way between the North Pole and the Equator– and a definite road trip must stop!

Derby Line, Vermont/Stanstead, Quebec

Derby Line and Stanstead are two towns built straddling the US and Canada border. There are streets that go directly from one country to another and even a building that sits right on the border– The Haskell Free Library and Opera House which was built as a symbol of friendship between the two countries. You can enter the building in the US and exit into Canada, passing through a patrolled crossing. You can also have your feet in both countries at the same time. Follow your GPS to the library and you will be there! I thought it was really cool, my husband expected border guards to come surround us the whole time. There is one imposing sign that suggests that, but the placards state that you can use the walkway to the library which crosses the border.

You can watch a video about our stop of a winter road trip to Quebec City:

Stops for your Road Trip from Boston to Montreal Through Vermont

Woodstock, Vermont

A stop in Woodstock will add about half an hour to your drive, but it is my favorite town in Vermont. Woodstock has a gorgeously charming inn, an upscale downtown full of restaurants and shops and covered bridges.

Read all about Woodstock, Vermont. 

Quechee, Vermont

Right near Woodstock is the village of Quechee. It has a gorgeous gorge to hike, lots of artisans to visit and cheese to taste. You can read about it in the Woodstock post.

Ben and Jerry’s Factory

Ben and Jerry’s ice cream factory is a needed stop for any road trip through Vermont. It has the hippy, local farm and artistry vibe that makes Vermont unique.

This famous ice cream factory is a place I return to whenever I happen to be in Vermont and it is right on the route between Boston to Montreal! Ice cream is one of my very favorite foods and Ben and Jerry’s falls in my top favorites for mass-produced ice cream.

Not only is there an ice cream bar with every flavor of Ben and Jerry’s possible, there are also other fun things to do here. For a small fee, you can see the inner workings of the factory (well, from a viewing platform). At the end you get to try a new flavor. After your tour, be sure to check out the flavor graveyard, where some of my favorite flavors are laid to rest. (Did you ever try Oats of This World?– I miss it!)  I would plan to spend between 1-2 hours here.

Warren Falls, Vermont

Getting some road trip peace in Warren, Vermont.

It will only add about 20 minutes to your drive to add these waterfalls to your Boston to Montreal itinerary. Not only will you be rewarded by natural swimming pools, but also multiple falls and a natural slide only a .1 mile hike off the road.

Crossing the Border Between the US and Canada

You will need a passport, whether you are walking or driving across this border. If you have NEXUS to help expedite your crossing, it only will help if everyone in your car has it. The lane is only open certain hours as well. Because I have it, but not my kids, we all had to wait in line.

As an aside, I have NEXUS as part of my Global Entry package, which was some of the best money I have spent to make travelling easier.

Pretty cool fact– The border between the US and Canada is the longest international border in the world!

You will have about an hour after you cross the border until you reach Montreal. I should add that is without traffic. Montreal has egregious traffic, so plan accordingly.

Read on to explore Montreal with us!

Also, if you keep driving about two hours more, you can get to Quebec, my favorite Canadian city!

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