Exploring Montreal and New England: A 11-Day Road Trip Adventure

When one of my favorite couples sent a wedding invitation for their stunning celebration in Vermont, I knew I had to go. Not only did I want to celebrate them, but it also felt like the perfect excuse for a summer road trip through some of the most beautiful regions in North America. I jumped at the chance and added nearby Montreal to the itinerary, along with stops in Vermont, New Hampshire, Maine, and Massachusetts!

Over 11 incredible days, we explored vibrant cities, picturesque towns, and scenic landscapes. Although we went in the summer, this roadtrip is known for its beautiful fall foliage and can easily be taken and tweaked for the perfect fall roadtrip as well. In this post, I cover everything we did on the roadtrip, along with what I'd highly recommend - and a few things I'd skip next time.

Part 1 - Montreal

Tips for Montreal

• Language: Please remember that the native language in Montreal is French! Majority of signs and menus will be in French. Although many locals speak both French and English, it is great to brush up on a few French terms to get around the city!

• Currency: Currency is in Canadian Dollars and I recommend getting some cash out from an ATM for local markets as we had some issues with U.S. cards charging vendors an extra fee so they asked for cash only

• Tipping: Tipping is very similar to the U.S. with 15-20% at restaurants, $1-$2 per drink at bars, and 10-15% for taxis/Ubers

Day 1 - Arrival in Montreal

After a long day of flights, we landed in Montreal in the afternoon for our first day. We hit the ground running by purchasing our STM passes to navigate Montreals public transportation to our hotel in Longueuil.

For only $20 CAD per person, we snagged 3-day passes that gave us unlimited rides on both the Metro and buses. Apple Maps became our best friend—it’s super easy to use for public transit directions, even telling us exactly which lines and stops to use. Pro tip: If you’re deciding between Google Maps and Apple Maps, we found Apple’s interface way more intuitive in Montreal.

We navigated our way to Old Montreal to Place Jacques-Cartier to take a ferry to Longueuil. The ferry is $5 CAD and can easily be missed on the docks. It is on the water and the last vendor at the end. The ferry also makes a stop at St. Helen's Island if you are interested in taking a stop along the way!

We arrived at our quaint hotel Refuge du Poete a family-run gem in Longueuil. It was budget-friendly with a homey vibe—complete with a welcoming dog named Coquette who loves greeting guests. There is a shared bathroom with other guests but we never had any issues with the bathroom not being available. They also offered a delicious free breakfast during our stay as well!

After settling in and dropping off our luggage, we took the ferry back to Place Jacques-Cartier for a delicious dinner at Trattoria Gio. It was a beautiful day and the restaurant has a great outdoor area to enjoy the weather and listen to the live music in the square. We wrapped up our first night by wandering the square and enjoying the many street performers and music!

Day 2 - Montreal

We began our day bright and early by grabbing coffee at Cafe Olimpico if you arrive early you can find great spots to sit by the open windows and people watch in the morning!

Caffeine fix completed - We then headed to Place Jacques-Cartier to meet for a free walking tour of Old Montreal. This tour was amazing and took us through the history of Montreal and interesting facts about the city. We took stops at Vaquelin Plaza, the Town Hall, Ramezay Castle & Gardens, Bonsecours Market, the Notre Dame de Bon Secours Chapel, Notre-Dame Basilica, Central Bank, the Royal Bank of Canada and a glimpse into the Underground City. My favorite part was the English Pug & French Poodle statues which represent the historical divide between the French and English Canadians each snubbing the other.

After our walking tour, we were starving and decided to use public transportation to check out the Jean Talon Market. This market is a foodie heaven filled with local vendors offering everything from fresh produce to pastries. We grabbed croquettes and a Spanish Omelette sandwich at La Croqueteria and macaroons at another vendor for a late-day snack.

All filled up on delicious food, we made our way to St. Joseph's Oratory, for fantastic views of the city and more knowledge into the history of Montreal. Entry into the church is free and well worth the visit!

We then navigated to Little Portugal for a look into Montreal's vibrant street art scene. The most iconic street is Saint-Laurent Boulevard which divides Montreal into east and west. There are plenty of stores and restuarants along the way to check out and you can spend hours wandering these streets.

Exhausted after long walks through Little Portugal we went back to our hotel to freshen up for the night and grabbed dinner nearby at Silva Grillades. This restaurant had delicious Portuguese Tapas and was a great quick stop before we took an Uber to The Comedy Nest for a show!

Montreal is well-known for its comedy being host to one of the largest comedy festivals every year, The Just for Laughs Comedy Festival. To get a sample of what Montreal Comedy had to offer we stopped in at The Comedy Nest for a great comedy show with a very, small intimate feel.

Day 3 - Montreal

For our last day in Montreal we went to Barley Bar à Céréales where we grabbed a delicious brunch and enjoyed the weather outside before getting back to exploring the city.

We decided to explore the inside of many of the stops along our free walking tour beginning with the Notre Dame Basilica. The Basilica began major restoration work in 2020, which will take over fifteen years to complete so it was still under construction during our visit, however, that did not take away from how beautiful the Basilica is on the inside. For the sake of time, we got basic admission tickets ($16 CAD, but we used student IDs to get discounted tickets for $14 CAD) to explore the inside, however, the Basilica is also well-known for its AURA experience ($35 CAD for standard admission), a night-time visual and musical experience that lights up the inside!

We then took a walk across the street into the Bank of Montreal, founded in 1817, making it Canada's oldest incorporated bank. There is a museum inside called the Bank of Montreal Museum that is free to visit, but being pressed for time for exploration we didn't get to explore that museum!

Next, we visited a heritage building that was once the Royal Bank of Canada and previously the tallest landmark in Canada built in the 1920s. It is now a coffee shop called Crew Collective & Cafe and offers an open coworking space, modern meeting and conference rooms, and private offices. The architecture here is stunning and it is an excellent place to wander and take pictures!

Right around the block, we took a break at Terrasse Place D'Armes, a rooftop bar at the top of the Hotel Place D'Armes with breathtaking views of the city! This place was a hidden jewel and had a great cocktail menu as well.

Continuing with the gorgeous views of the city, we made our way to the Notre Dame de Bon Secours, one of the oldest churches in Montreal, built in 1771 over the ruins of an earlier chapel. A visit to the chapel is free, but I highly recommend paying for admission into the museum for a great experience ($14 CAD for adults standard admission, we used student IDs for discounted tickets at $7 CAD). The museum is dedicated to Marguerite Bourgeoys who founded the chapel and dedicated her life to supporting her community.

After exploring the Notre Dame de Bon Secours, we grabbed a snack at Cafe des Arts inside the Marche Bonsecours. The Marche Bonsecours has plenty of shops and vendors to check out along the way! Especially if you are visiting on a rainy day like we were and need some time to get out of the weather.

Knowing we were taking a late night Greyhound bus to our next destination, Burlington, Vermont. We headed back to our hotel to grab our luggage and stopped in at L'Amère à Boire, a pub right across from the Greyhound bus station for a quick beer and snacks!

We then loaded on to our bus for an overnight trip to Burlington, Vermont, taking one stop at the border for a quick questioning with the border patrol before continuing on our journey.

Part 2 - Vermont/New Hampshire

Day 4 - Vermont

After a long night on the Greyhound bus we arrived at 3 a.m. in Burlington, Vermont and caught an Uber to our hotel to check in and sleep for a few hours before grabbing our rental car from the Burlington Airport for the rest of the trip. After sleeping in for a few hours, we had some time to explore Burlington before heading to Burke for our friend's wedding.

Luckily, we arrived in Burlington on a Saturday where Burlington's Farmer's Market was in full swing. We sampled our way through so many Vermont treats there including Kougn Amann at Slowfire Bakery, Maple Kettlecorn at Karen's Artisan Popcorn, Maple Lemonade at Theo's Maple Lemonade and even having a Maple syrup tasting at Silloway Maple. Although a few vendors accept Venmo, know that the best payment method here is cash!

We couldn't leave Burlington without trying out legendary Maple Cremees, taking a stop at Burlington Bay Market & Cafe before taking our Maple Cremees for a walk along the Burlington Bay. It was a fairly rainy day that morning, so we took a quick drive down the street to take a quick glance through the shops and scenery on Church Street!

We then loaded up to head out of Burlington to our hotel for the night, the Burke Mountain Hotel. The hotel offers absolutely beautiful views of the Vermont mountains very close to Lake Willoughby. We quickly got ready and took the shuttle to the highlight of the trip - Our friend's wedding on Lake Willoughby.

Easily, one of the most beautiful weddings I've ever been to on a very small and intimate location on the lake. After a long night of dancing and drinks, we were absolutely exhausted and crashed for the night, ready for a long next day roadtripping through Vermont and New Hampshire.

Day 5 - Vermont/New Hampshire

This day was easily one of our most packed travel days, getting up early to explore the nearby cities of Stowe and Waterbury. Our first stop was Cold Hollow Cider Mill for the most delicious apple cider doughnuts and hot apple cider. There is a small museum in the mill that is self-guided and brings you through the full process of creating the apple cider.

We then headed out for an easy, short hike at the nearby Moss Glen Falls! This short hike is well worth it for the beautiful views of the falls, we went early on a Sunday and it was very quiet. The parking lot is very small but we had no issues with parking! The Trail is free and open to the public year-round. Be careful walking on the path in some areas if it has been raining as some areas can get muddy and if you're clumsy (like me, unfortunately) you may slip a little)

Before continuing on our way to New Hampshire, we took a stop at a well-known covered bridge, the Gold Brook Covered Bridge or better known as "Emily's Bridge." This bridge was built in 1844 and is well-known because of it's legends of being haunted by a girl with a broken heart over being jilted by her lover who took her own life. We didn't experience anything spooky while there, but it was still a very neat spot to see a local covered bridge over a beautiful river.

We then began the drive to Franconia, New Hampshire for a few hikes along the way. We made the quick hike up to Artist's Bluff to see stunning views of the White Mountains and Echo Lake. On our way back from this hike it began pouring raining so we weren't able to do as much hiking in Franconia as we would have liked to, but there are plenty of beautiful hikes to explore in the area.

We then drove to the Kancamagus Highway for scenic views for the rest of our drive. We made several stops along the way to see the Rocky Gorge Scenic Area, Sugar Hill Scenic Area where we saw a beautiful rainbow, and the Lincoln Woods Suspension Bridge. The Kancamagus Highway runs through the White Mountain National Forest and is considered one of the best places in the world to see the fall folliage. Although we didn't see the fall folliage on this trip, we were blown away by the beauty of the White Mountains!

We arrived in Conway for the night and stayed at an amazing Mountain View Studio Airbnb. We loved this Airbnb and wished we could have stayed longer! After a long day of traveling we were starving for a big dinner and made our way to Chef's Bistro in North Conway. Restaurants close very early in Conway so when trying to find food options make sure to check on hours before going!

Part 3 - Maine

Day 6 - Maine - Acadia National Park/Bar Harbor

We began our day by grabbing breakfast in North Conway at Peach's Restaurant. This was an adorable and small cafe with absolutely delicious breakfast! On our way out of Conway, we made a pit stop at a Walmart for snacks and sandwiches to pack for the road and our hiking in Acadia National Park.

After a little under 4 hours of driving we were very excited to stretch our legs and begin exploring Acadia. We made sandwiches and relaxed by finding a quiet spot on some rocks surrounded by the ocean. Our first views of Acadia were stunning and I could spend hours on the rocks just watching and listening to the waves crash, but with so much to see in the park and so little time we decided to take a short walk around the Jordan Pond Path for more beautiful views.

After soaking in the beautiful views, we made the drive to our Airbnb which is very conveniently located inside the park! This Airbnb rented a room inside our host's home. We absolutely loved our host and her sweet dog, Appa. She gave us plenty of recommendations for places to visit during our stay! Following her recommendations we drove into Bar Harbor for dinner and drinks at Black Friar's Inn & Pub. We loved this place and the food and location was amazing.

After dinner we took a walk to the Bar Island Sand Bar for sunset. I can honestly say, I've never seen such a beautiful sunset, the sky looked like it could have been painted. Depending on the time of the year, make sure that it is low tide before visiting!

Day 7 - Maine - Acadia National Park/Bar Harbor

We started our morning VERY early in the first place that sees the sunrise in the U.S., Cadillac Mountain. We got there at 4:45 a.m., but it started getting light much earlier at 3:45 a.m. so I recommend getting there as early as possible. Cadillac Mountain is very popular and you need to reserve a vehicle permit for sunrise through the website. 30% of the Cadillac Summit Road Sunrise reservations are available for purchase 90 days in advance of the reservation date and the other 70% are available for purchase at 10 a.m. ET two days in advance of the reservation date. We made our reservation through the NPS Website two days in advance and had no issue getting tickets! The sunrise at Cadillac Mountain is absolutely worth the early wake up time. The views are spectacular!

After Cadillac Mountain, we checked out Sand Beach and then hiked the nearby Gorham Mountain Loop. This was a mild trail with beautiful views of the park and a great substitute for the Bee Hive Trail which offers similar views!

We took a stop along several of the Ocean Path Trail spots including Boulder Beach, Otter Cliff Overlook, Otter Point Overlook, and Otter Cove Overlook. We then headed over to Thunder Hole which is a carved out inlet along the rocky eastern shoreline of Mount Desert Island. When a turning tide forces waves into this narrow channel, the air escapes with reverberation that sounds like thunder! It is recommended to get here 1-2 hours before high tide and we arrived early to check out the sight. We did not get the Thunder Hole experience, but the views were beautiful so we still enjoyed relaxing and watching the waves.

Hungry for some food we took a pit stop at the Jordan Pond House. The Jordan Pond House is famous for their "popovers" which are a light roll made from an egg batter similar to Yorkshire pudding. This a very popular tourist spot with the first popovers and tea being served here back in 1895, it is also a very important historical spot in the park. This place gets very packed so make sure to make a reservation or be prepared for very long wait times!

After stuffing ourselves on popovers we took a trip to the Bass Harbor Head Lighthouse. A Coast Guard's family currently lives here so you aren't able to tour the inside, but you can see the beautiful views of the cliffs from here and the lighthouse!

We then took a drive back into Bar Harbor to explore the local shops, the Harbor views, and get ice cream at Mt. Desert Island Ice Cream. After a long day of exploring, that ice cream was just what we needed!

Day 8 - Maine - Portland

Before heading to our next stop on the trip, we fueled up with some coffee and pastries at Sunrise Cafe on the docks of Bar Harbor! We had a long 3-hour drive over to Portland and hit the ground running with a spot I was thrilled about - The Holy Donut. My mouth waters just thinking about these donuts! Made from potatoes (you read that right), they are prepared fresh daily using wholesome, high-quality ingredients. The Holy Donut is a must-visit spot while in Portland!

We spent some time exploring the city and took a walk across the Casco Bay Bridge. Before heading to our Airbnb we tried to take a pit stop at the Two Lights Lighthouse, but thick Maine fog rolled in, making it very difficult to capture clear pictures!

We checked into our Airbnb for the night before taking our hosts recommendation and heading to Highroller Lobster where we had our first Lobster Rolls and Maine oysters! There are two styles of lobster rolls: Maine lobster rolls, served cold and tossed in mayonnaise, and Connecticut-style rolls, which are warm and dripping with savory melted butter. We decided to try them hot for this first attempt and they absolutely did not disappoint!

Not ready to end the night, we stopped at Luna Rooftop Bar for drinks with incredible views of the city before relaxing and heading back to our Airbnb for the night.

Day 9 - Maine - Portland

With a long day of sightseeing ahead, we stopped in at Dutch's for an amazing diner-style breakfast. We then embarked to see Portland Head Light and the Portland Breakwater Lighthouse, also known as "Bug Light." These lighthouses were amazing sights to visit and see!

With some time to spare, we wandered the downtown shops and stopped for drinks at The King's Head, an intimate gastropub with a warm ambiance! We then caught a ferry to Peaks Island to explore the island, grab ice cream, and check out a very interesting and quirky Umbrella Cover Museum.

With more plans for the night, we stopped in for an early dinner at Luke's Lobster to try cold lobster rolls. These lobster rolls were delicious, but I think the hot lobster rolls will butter are what really claimed my heart here!

Portland's coast is dotted with smaller islands known as the Islands of Casco Bay. You can take the Casco Bay Lines to a single island, or for a broader view of the bay, opt for a sunrise or sunset Mailboat run. We decided to do a sunset Mail Run Cruise which was a 2 1/2 hour journey showcasing many of the islands including Long Island, Cliff Island, Chebeague Island, Diamond Cover, Great Diamond Island, and Little Diamond Island. We also got to see the smallest lighthouse registered with the U.S. Coast Guard, the Echo Point Lighthouse at only 6 feet tall! It can get very chilly on the water as the sun sets, so make sure to bring some extra layers to stay warm.

Part 4 - Boston, Massachusetts

Day 10 - Boston, Massachusetts

We woke up early, grabbed coffee and breakfast sandwiches at Tandem Coffee & Bakery in Portland, and hit the road to Boston! I've visited Boston before, but was very excited to check out a few spots I hadn't been able to visit on the first trip.

After just under 2 hours, we arrived in Boston and checked into our hotel for the night at the Element Boston Seaport Hotel. After dropping off our luggage we headed over to the Christian Science Publishing Society to see the Mapparium - a three-story-tall globe made of stained glass that is viewed from a 30-foot-long bridge through its interior. It was built in 1935 and although the globe was created to change with changes in territories, the decision was made to keep the globe as a permanent picture of the world in 1935.

The architect, Chester Lindsay Churchill, created a highly accurate globe that reflects the relative sizes of the continents. With a view from the very center of a globe, looking out, the eye is the same distance from every point of the map, preventing distortion of the surface of the Earth. You can still find countries like Siam and French Indochina, but Israel and Indonesia do not exist on this map. You can hear your voice in full 360-degree surround sound if you stand in the center of the globe, but if you stand at one end of the bridge you can hear the whispering of anyone who is at the opposite end. Tickets to this exhibit are only $6 and it is well worth a stop!

We made a quick stop at Tatte Bakery next door for a snack and coffee before heading back to the hotel to freshen up for dinner. We took an Uber to the North End and managed to snag last-minute reservations at Cantina Italiana for delicious Italian food and wine!

Next, we headed to Warren Tavern for after-dinner drinks and a taste of Boston history. Built in 1780, Warren Tavern is the oldest tavern in Massachusetts and was visited by many famous faces including George Washington and Paul Revere. This was a great spot to soak in Boston history while getting a glimpse of the local sports culture, as it's now a popular spot for cheering on Boston teams.

Located nearby is Bunker Hill, famous for the Battle of Bunker Hill where New England Soldiers faced the British army for the first time in a pitched battle. We visited at night so we weren't able to get the full experience, but there are many plaques about the history of Bunker Hill along the way!

Day 11 - Boston, Massachusetts

Since it was our last day of the road trip, we woke up early to pack in as much as we could! We began with a drive to the Harvard University campus and a delicious, filling breakfast at The Friendly Toast. After a hearty breakfast, we needed to walk off all the carbs, so we took our time exploring Harvard's campus, including Harvard Yard, Memorial Hall, and Cambridge Common.

We then made our way to the Boston View Sky Deck at the top of the Prudential Tower which offers 360 views of the city and has a Bistro & Bar inside with views of the city. Personally, I think it is overpriced for the time spent here, but the views of the city were beautiful!

We ended our trip on a high note by relaxing at Boston Common, which was in full weekend swing with live music, picnickers, and ducks swimming in the ponds. The Boston Commons never gets old and if you are a movie nerd like me it is actually the filming location for several scenes in Good Will Hunting!

After a long trip packed with adventures and so many beautiful landscapes and experiences, we made our way to the airport to return our rental car and begin the long journey home. This trip was one of my favorite roadtrips and even though it was a longer one for me, I wish there was so much more time to explore these beautiful cities even more. I hope that this roadtrip guide helps inspires you for your future roadtrips too!