Long Weekend in the Northeast: Itinerary

Finally, I had the time to sit down and write about our Northeast Road Trip Extravaganza. I recommend visiting in the fall for obvious reasons (leaves, crispness, etc.) but I could see this being an awesome spring or summer weekend trip. Winter for sure if you’re psychotic and enjoy being outside when it’s cold.

The shortlist for our itinerary was as follows, but please note I don’t recommend it. We were pretty rushed, and with early sunsets, we didn’t get to see as much of the towns as we would’ve liked.

  • Day 1: Fly into Boston, spend day/night in Burlington, Vermont
  • Day 2: Burlington, Vermont in morning, drive to Montreal for afternoon/night
  • Day 3: Montreal, Quebec in morning, drive to Portland, ME for night
  • Day 4: Portland, ME, Portsmouth, NH, and Salem, MA on the way back to Boston

Instead, look at these options:

If you have four days: Boston → Burlington, Vermont → Portland, Maine → Boston
If you have five days: Boston → Burlington, Vermont → Montreal, Quebec → Portland, Maine → Boston

For both trips, I do recommend stopping in either Portsmouth and/or Salem on the way back to Boston. They’re such charming towns that won’t add much stopover time to your trip back. Now! Let’s get into the highlights of our weekend trip.

Burlington, Vermont

While I dedicated a whole post to this magical city here, I’ll give you the lowdown. Burlington is Vermont’s biggest city, with a mere 42,000 people. The town is centered around Lake Champlain, an area our weather didn’t allow to us enjoy, but that I heard thrives in the summer.

We drove straight from Boston, winding through New Hampshire (a SERIOUSLY underrated state) and Vermont’s rolling mountains. Renting a car this trip is a must– not only are the views gorgeous, but I’m not sure the trip is doable without it, lol.


Ben and Jerry’s Factory Tour – Our first stop was one of Vermont’s most well-known and best tasting attractions. The tour was pretty good for its low price tag, and honoring the creators in their hometown felt pretty cool. It’s hardly out of the way to stop on the way to Burlington, so if you’re coming from Boston, I’d definitely recommend.

Around Burlington – If you’re visiting in the summer, take the time to see Lake Champlain. If not, Church Street is beautiful rain or shine. This tree-lined street is quintessential Burlington and is packed with shops, restaurants, coffee shops and more. I could’ve spent hours taking photos strolling around.

Food and Drink

American Flatbread – A hippie, homey, wood-fired pizza place with great local beer offerings and veggie specials. SAY. NO. MORE.
Citizen Cider – For those who are into cider and those who are not, you will enjoy. I never thought I wanted basil-flavored cider, but boy did I ever.
Feldman’s Bagels – Because brunch is overpriced and bagels are underrated.

More recommendations on my post, here!

Montreal, Quebec

Boy, Montreal, you ended up being out of the way, but I’m sure glad I met you. Now, I have to preface, you know when you go somewhere and it feels like everything about the place is against you? The weather, the festivities that are happening, etc.? That’s kind of how Montreal was for us. We got rainy, gloomy, and cold weather (which I actually hear is pretty common- so I’m not sure I should be complaining), and one of the main walking areas that was known for its charm was under construction.

Looking past the obvious annoyances, I could see what people loved about the city. Montreal is a modern city mixed with areas that felt straight out of Europe. Think: cobblestone streets, grand churches, and detailed architecture that you just don’t get in America. The fact that most people were speaking French probably contributed to that feeling as well, haha. It was a cool feeling, though, driving less than two hours north of Burlington and practically being transported to France.


Our activities, like in many European cities, involved walking around, admiring the architecture, and of course, finding food the country was known for. In this case, poutine, a dish with french fries covered in cheese curds and gravy.

I recommend walking around Old Montreal, specifically Rue Saint Paul. On our second day, we spent time around the Mile End area of Montreal, more of a hipster neighborhood (that was home to my favorite meal of the trip, below)

Food and Drink

Olive & Gourmando – We came here for coffee and pain au chocolat, and I would like to go back every day for the rest of my life. I’ve heard great things about the paninis, but I think you’ll score regardless of what you order.
Tsukuyomi – This was the real winner of the trip. I dream about this ramen. And because ramen is inherently a meat-based dish, you’d think you’d miss out getting a vegan ramen. BUT NO! Simply phenomenal.
The Cold Room – There’s just something about speakeasies in Montreal. We had so much fun searching for the entrance, and were greeted and brought to a dim but chic basement, if that’s a thing. My server even custom-made a spicy drink for me because I’m an asshole. Five stars.
L’Orignal – Everyone was pleased with their food here, but it wasn’t mind-blowing, and that’s what I’m looking for always.

Portland, Maine

I’m all about precursors here, and for Portland, my precursor is that I could absolutely see myself living here. I am PARTIAL to Maine now, and that just means I enjoyed it, so I’m going to continue to give my recommendations.

We drove to Portland from Montreal which was not necessarily a FUN ride in the dark, but boooooy this is where New Hampshire comes back into play. We drove through the White Mountains, passed through the most quaint little towns, and I almost cried of its beauty. Don’t let people rip on New Hampshire, you guys. I’m about to plan a trip back to the MOUNTAINS where I BELONG.

Anyway, back to Portland. It’s not the capital of Maine, but it’s the SPOT, ya know? There’s lobsters, and cobblestone streets (we are in New England, of course), and poutine again, some more seafood, and great, great beer. The people were laid-back and friendly. I felt like everyone in town was a childhood friend that had that mutual feeling of knowing better than to say hello to you in public. Does that make sense? They were cool with us being there, but did their own thing, and everyone was okay with that. On to the good stuff:


Walk around Old Port – Old Port, or the downtown area, is a beautiful mix of New England coastal charm with Portland’s artsy vibes. This is a popular walking area for tourists, but didn’t feel touristy at all. Give yourself a couple hours to browse shops and stop at the Holy Donut, which I will cover below.

Allagash Brewery Tour – There’s many reasons this should be on your list, and they’re as follows: 1) it’s beer, 2) it’s free, 3) and it’s actually super interesting. They don’t skimp on time here, and you’re given a FULL tour, as this building does everything from the brewing to the bottling and shipping. Remember to book ahead as slots fill up quickly– we had an 11am tour (not complaining though, lol).

Portland Headlight/Ft. Williams Park – I’m a liiiiittle pissed I didn’t get to see a proper lighthouse while in Maine, but you can’t win them all. This is one of the closest and most popular lighthouses to visit while in the area.

Food & Drink

Eventide Oyster Co. – Home of one of the most famous lobster rolls in Portland, as well as, you guessed it, oysters. Mostly a seafood place, we all loved our dishes– and there was vegetarian specials for all you fellow veggies out there. Grab a drink at a dive bar called Tomaso’s Canteen while you’re waiting and MAKE SURE your table is ready before you leave : )
The Holy Donut – As a Chicagoan (or really any big city lover), I have an affinity toward donuts, specifically funky ones. The Holy Donut makes donuts out of fresh Maine potatoes, giving them a rich, moist (ha!!!!) texture. Combined with their fun flavors, this was one of my favorite stops of the trip. Highly recommend.
Lincoln’s – Another speakeasy because they’re way more fun than walking into REGULAR bars! This one was tough to find, but we did with the help of a local who was more than willing to watch us look like idiots walking into back doors of random establishments. The kicker: everything is $5! Again… say no more. (Bring cash) (Thanks, Zack, for this recommendation).
Bite into Maine – We stopped here on the way out for one of Portland’s acclaimed lobster rolls. People argue this is one of the best.

Others that we didn’t see that I would’ve liked to:  Duckfat, Central Provisions, Hot Suppa

Portsmouth, New Hampshire & Salem, Massachusetts

On our way back to the Boston Airport for our flight, we took two little detours in Portsmouth, NH and Salem, MA. I had coached a cheer camp in Portsmouth a few years back and remember how much I loved the town, so we did a 30 minute stop in the harbor town. I’ll let the photos speak for itself.

Salem was an obvious stop, as we were in town October 30th. If you’ve seen Hocus Pocus in the last five years (I hadn’t) you’ll absolutely love it. However, I’ll never complain about a New England town in the fall, and that’s a fact.

Have you visited any of these places? Hopefully! Did I miss some major spots? Most likely!

Thanks for listening to my rants of excitement and amateur food reviews,

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