6 States and 1 Province, 1 Week

Sometime last year, my fiancé told me he wanted to go to Montréal for his birthday. My first thought was “hell yes”. I have been wanting to visit mini-France ever since I learned that the native language in Montréal is French. 

As I thought more about it, I came up with this northeast road trip idea. We would make Montréal one of the stops along the way. 

Next thing you know, our road trip was born.

If you are curious about the northeast, especially the “New England” area, this post is for you. Be warned, you are going to want to plan a trip ASAP after reading this.

Day 1 – Rhode Island

Saturday. It’s 3:30am and I just called lyft to take us to the airport for our 6:45am flight.

We started our 6 state, 1 country road trip journey in Providence, Rhode Island. The weather is OK. Mid 40s. No Sun. But good photo weather.

Our first stop is a diner in East Greenwich, Jigger’s. I had the most amazing breakfast. Probably my second favorite of the trip, my first favorite was in Vermont!

First meal of our trip. Delicious! At Jigger’s.

Chili and cornbread eggs benedict. AMAZING! My first thought after that bite of food was “this is going to be a long week”.

We stayed with one of my colleagues in RI. She took us down to Newport Beach where we had lunch at a restaurant on the pier and took a beautiful stroll around the Cliff Walk.

Dinner was in the downtown area of Providence in their Little Italy area. Apparently Providence has some really amazing Italian restaurants.

After dinner we headed to The District to meet one of Julian’s friends. This place is the hangout for the culture in Providence. They had a live band that was playing a version of Ginuwine’s Pony that had me dancing in my bar stool.

I give Providence a B –


  • Beach town. Good walk-able areas. 
  • Cuisines selection is pretty decent. 


  • Very little diversity. Downtown area is meh. 

Don’t get me wrong Rhode Island is a beautiful, but compared to our other stops, this one was my least favorite.

The best part of this stop was spending time with my friend/colleague, her husband and their adorable 2 year old. He was my shadow for the 36 hours we spent in Rhode Island. I loved having him as my tour guide.

Day 2 – Massachusetts & Upstate New York

Drive time: 1 hour 30 minutes to Springfield.

So full disclosure, we never stayed in Massachusetts our entire trip. But we did have to pass through it twice, ones going to Saratoga Springs and then going to the airport.

The only reason I even counted it as a stop is because we did stop in Springfield, Mass to check out the NBA Hall of Fame museum.

We. Were. Not. Impressed. At. All.

For this to be a Hall of Fame museum, there were a ton of exhibits that were under construction or not working.

There was no Micheal Jordan shrine. We barely saw sneakers. And I didn’t see a good use of technology. We should have been bombarded in videos and recordings from historic games over the years.

“It was not an immersive experience” is what Julian says. “The best part is being able to play basketball at the end.”

NBA Hall of Fame: C-

Next stop Saratoga Springs, NY. Drive time: 2 hours

We. Were. Impressed!

BUT, this is the only stop on our trip were we ate at a restaurant that we did not like – Henry’s Street Taproom. We must have looked at the menu 5 or 6 times thinking something else was going to jump out at us, but nothing did.

I ended up with a dry biscuit and Nashville hot chicken. And Julian got a loaded grilled cheese that he ended up sending back. But to say the least, our company made up for it.

One of Julian’s former colleagues lives in the area. So we met up with them for some day drinking, try Max London, and later we had a Game of Thrones watch party for the season premiere.

Happy 37th to my Love!

Luis & Evelyn have a son who shares the same birthday as Julian. So they bought a cake for them to share. We sang Happy Birthday and dug in.

I give Saratoga Springs, NY a B++


  • The walk-able downtown area is great. Tons of cool shops to casually walk in and out of. 
  • Great cocktails and lots of restaurants to choose from. 
  • Apparently they have a good nightlife. Julian’s friends were out the night before until 2:30am. Did I mention they have 4 children? #goals


  • Again, very little diversity. 
  • No real scenery. Water is about 30 minutes away. 

Day 3, 4 & 5 – Montréal, Quebec

Drive time: 3 hours

Montréal is beautiful, hands down. It’s like being in mini-Paris. Everything is in French. Everything!

But the good part is that about 60% of the population speak both French & English. So after the bonjour, we say “Hi” and then the conversation turns into English.

The best parts of Montréal for me was the Fine Arts Museum, Mt. Royal & the bread! Ahhhh the bread!

The Montréal Museum of Fine Art had an out of this world fashion exhibit that featured the most iconic couture designs from the world’s top designers and highlighted some Canadian rock stars as well.

The structure, beading and design of these pieces just had my jaw permanently open for almost 2 hours.

Mt. Royal is about a 15 minute walk “up” the slope of mountain. Some reviews say you hike up a mountain to get there. You could, but we drove up and parked in a visitors parking lot and walked to the lookout point.

The city is gorgeous.

If you visit make sure you take a stroll through Old Montréal, that really will give you a European vibe with the architecture of the buildings and the cobble stone streets.

I give Montréal an A.


  • Food options galore. They have a Chinatown with some amazing Ramen options. Try Kinton Ramen near Rue Bishop. 
  • Mostly everyone speaks English. 
  • Coffee Coffee and more Coffee! The cafes available are great. 
  • Melting pot of culture. 
  • The Metro (train) moves at lightening speed. And not to mention hella clean. No need to rent a car if you are just visiting this city. Their public transit system is good. 
  • Lots of walking. Plenty of things to see and do. Make sure you visit Notre-Dame! 


  • The city is under major construction, everywhere. If you plan to visit in the next 12-24 months be prepared for a lot of detours and road closures. I felt like every block had something going on. 

Day 5 & 6 – Vermont

Drive time: 2 hours

I didn’t think the trip could get any better after leaving Montréal that Wednesday afternoon. But it did.

We arrived in Downtown Burlington around 4pm. It was about 63 degrees with clear skies and a beautiful sun.

Downtown Burlington sits on what you would think would be an ocean coast. That is how beautiful Lake Champlain looks. When we were walking through Waterfront Park, I thought I was starring out into the sea. But the mountains of upstate New York remind you that you are not.

After walking through park we started our stroll through their quaint downtown area. Boutique shops. Local Eateries. Bars.

After dinner with Stevie G from my Georgetown program we were walking back to our car and we randomly stumbled into a comedy club. They had just started an amateur comedy night.

The spontaneity of this trip is what made it so enjoyable. We had no rules or true plan. The fact that we just walked into a comedy club and sat there for an hour when were “supposed” to be going home was thrilling. It made the cheesy comedy even more hilarious!

I give Vermont an A+


  • Beautiful views. Park on the water. Bike friendly. Rentals available. 
  • Local eats. Prideful that food is from the region. 
  • Ben & Jerry’s
  • Diversity in the city 
  • Great vibes even for a Wednesday afternoon/evening 
  • Delicious drinks!


  • Can’t think of anything. I wish we had more time here. 
  • Oh and the locals say it gets -20 here in the winter. 

Day 6, 7 & 8 – Portsmouth, New Hampshire & Portland, Maine

The next morning we had breakfast at Vermont staple, Skinny Pancake – Delicious. They substitute actual pancakes for variations of crepes. Um Yum! I had a cinnamon sugar one. And their coffee is delicious. My favorite breakfast of the trip.

Best breakfast! Skinny Pancake in VT!

After our goodbye to the killer view we hopped into the car to head to the Ben Jerry’s Ice Cream Factory. Drive time: 30 min

Nestled in Waterbury, VT is where all of the delicious ice cream is made and shipped out. After our short 30 minute tour, it consist of a 6 min video and a tour of one room, we got a free sample of Cherry Garcia, I passed, and then headed out to get a scoop.

They had flavors I had never heard of before. Julian got a chocolate chip cookie dough milk shake and I had a flavor called CinnaDOUGHrella with chocolate sprinkles.

Next stop was Route 1A in Hampton Beach, NH. It’s their northeast version of the PCH.

Drive time: 3 hours 15 minutes

Driving up the coast of New Hampshire is beautiful. Make sure you add this to your list. It does add an extra 45 min – 1 hour onto your drive to Portland, but it is worth it. The gorgeous homes, view and waves make up for it.

There are plenty of places to pull over and take pictures.

Next we stumbled into downtown Portsmouth randomly.

Pause. Funny story: Julian thought some college basketball tournament was happening in the city and he was navigating us to buy tickets. It was trying to take us to Portsmouth, VA and not Portsmouth, NH. Ha!

So now we are walking through another cute downtown area. We see a sign for a African American museum. Of course we are going. But right when we walked up they were closing. It was 5pm.

The museum representative saw the disappointment in our faces, so she mentioned their was a slave burial ground memorial that we should check out around the corner. We went.

To our surprise, Portsmouth has a Black Heritage Trail that guides people through areas of the city where Blacks were using to escape slavery. We even found out that Fredrick Douglass has some history with Portsmouth.

We followed the Black Heritage Trail signs to a local winery. We stopped in for a tasting and a bottle of wine to take to our AirBnb.

On to Portland we went. Drive time: 55 min

Our first stop was Duckfat. This is a Portland staple. You have to visit. The fries are amazing and the sandwiches are delicious. Do not go here expecting to get a roasted duck breast entree. But what you will get is some amazing truffle fries, and killer roasted duck breast and arugula sandwich.

The Fries! It’s what everyone goes for.

One thing I am thankful Julian and I did was have down time. We did not spend the entire day walking through cities. We made sure that we spent time cuddle up on the couches of our AirBnb’s binge watching TV shows. We discovered Good Girls & On My Block while on our road trip.

The rest of our time in Portland was spent in coffee shops, trying on wedding bands. Buying socks and random trinkets. Visiting bookstores and the library. Drinking at 11am. And eating lobster rolls.

Downtown Portland has enough shops and restaurants to keep you active all day. Make note that none of the local retail businesses open until 10:30/11am. We are early risers. We were out the door by 9:30am to walk to get coffee and breakfast.

But once the doors opened, we walked in probably 20-25 different stores.

We had drinks and apps at Central Provisions. Lobster Rolls from The High Roller Lobster Co. And a delicious french inspired dinner from Five Fifty Five. Then more drinks at the late night popular Jewel Box.

The vibe in Portland was unreal. I saw Black Lives Matter signs in windows of several establishments that had all white employees. Diversity signs and Pride flags were everywhere. Everyone was so friendly. People spoke or nodded their heads at you where ever you went. And not just the Black Nod. I’m talking everyone is making eye contact and saying hey.

We were digging it.

And the nightlife is Portland was active. After our dinner at 555 we were walking to meet Julian’s friend who lives 30 minutes north of the city. We saw packed bars and several nightclubs preparing for the upcoming action.

Even the bar were were at, Jewel Box, had 90s Hip Hop and R&B on the speakers. As I was sipping my Mother of Dragons drink, yes they had GoT themed drinks, I was telling Julian, this place is my kind of vibe.

The next morning was our final day. We had just spent 7 consecutive days driving and exploring the northeast area of North America. We did not want it to end. But we had one more stop. Back to Portsmouth, NH.

We headed back to the Black Museum that was closed and then we hit up a game shop. I discovered the game Magic while we were in Saratoga and I wanted a similar game so we picked up a GoT card game. Total Nerds!

Our final stop was meeting up with one of my friends, and former colleague, for brunch and $1 oysters. We ordered 48 between 4 of us.

$1 oysters at Row34 in Portsmouth, NH

As we were driving though Boston to get to the airport, both of us felt the tension of being back in a major city again. We had just spent an entire week, Saturday – Saturday, small town living. Minus Montréal.

Drive time to Boston Airport: 55 minutes

I give Portsmouth an A


  • Walk-able. Black History exhibits. 
  • Local eats and wineries, seafood!
  • Beach is 15 minutes a way 
  • 1A – Coast driving 


  • Not much diversity. But people are pretty friendly. 

Portland gets an A++


  • Everything. Every damn thing.


  • It’s so far away! 

This was probably one of the best experiences that I had ever had. There was not a better way to explore the Northeast than by car. You see much more.

If you want to take this trip, or any road trip, here are a few final tips you should remember:

Mix up your accommodations. Do not stay in a hotel for this entire trip. My suggestion is stay in an AirBnb for those stays that are more than 2 nights. It mixes up the vibe. And then when you want down time during the day you do not have to lay in a bed. You can sit in a living room. You also get a local neighborhood feel. Which makes the trip even more homey.

Don’t skim. This trip can get pricey with 2-3 full meals per day. Accommodations each night. Gas. Tolls. Activities. Etc. But try hard not to be cheap. When will you ever get to visit all of these places at one time again. The experiences that you will have on this trip will be memorable. So order that lobster or that $15 cocktail. Live it up. Just plan accordingly.

Don’t over plan activities. We didn’t have many plans for our trip. We knew we wanted to try coffee in each city and visit the Ben & Jerry’s Factory in VT. Other than that we had no plans besides seeing friends at every stop outside of Quebec. By us not planning any activities it gave us the freedom to randomly have plans.

It was the best feeling waking up in the morning with no plan for the day. Have you ever tried that. It’s so freeing. You should try it.