During the first weekend in October (Columbus Day weekend) I went on a little adventure in New England! Read more below about my fall travels in Vermont and Maine.
Part 1: Vermont
I flew into Boston and my friend Jo picked me up so we could head to Springfield, VT for the long weekend (she and her husband had Columbus Day off, and now that I work for myself, so did I). On the way we stopped in Manchester, NH for lunch, which was perfect because 1) we were hungry and 2) I’ve never been to New Hampshire, but now that I’ve eaten there I think that counts (so now I’m up to 36 states visited!).
Our home base for the weekend was Springfield, but we ventured into other small towns throughout the weekend. To give you an exact rundown of everything we did seems nearly impossible at this point as there was never really any agenda, just a loose checklist of things we wanted to do or see or places to go to.
What I loved about Vermont was the general vibe there. Everything is old (compared to the Midwest) and beautiful and lush. All of the roads are tree-lined, may of them winding, and there’s even a mountain or two (more like giant hills, but we’ll let them call them mountains). Things just feel more laid back in Vermont. It takes a minimum of 10 minutes to get to the next town, but often you drive a bit further to get to your favorite shop or restaurant. And because of this, nothing ever felt rushed. We didn’t really have an agenda over the weekend. It was the perfect opportunity to just unplug and enjoy life. Which is what we did.
Jo and Gus both understand my love of food, so there was plenty of it over the course of the weekend. The first night there we went to dinner at this cozy spot called Stone Hearth Tavern in Chester. We grabbed lunch at Moon Dog (to go), which is one of Jo’s favorite spots, and I can see why. The menu is super fresh and healthy – they make everything out of this adorable kitchen space. But they have this old cabinet full of pastries and we snagged a couple of crumb cakes for breakfast the next day.

We visited Meditrina, a quaint wine and beer shop in downtown Chester, which is owned by a friend of theirs. The highlight of our wine shop visit was a brief education in French wines – I learned that I’m crazy about Gamay! And I also learned that I need to do a lot more research about wines.
We also came across this placed called Vermont Cannoli and yes, we went in, and yes, we got cannolis, and no, that is not how you pronounce my last name. The inside of the shop looks like someone’s small kitchen. They make the filling and shells somewhere else but assemble and sell them there. They were amazing.
So we ate out some but I also got to cook for them in their beautiful old kitchen! Jo eats vegan so I made chili two ways: black bean and sweet potato for her, added ground turkey for Gus and me. And I attempted a fancy apple pie, which ended up tasting much better than it looked.
The coolest part about cooking in their kitchen is this fantastic old stove. It has a tiny oven in the upper right quadrant, then 4 drawers of storage space. And the buttons all light up different colors like a mission control center. I’m usually a gas stove kind of girl, but I didn’t even mind because this stove was so cool.
Also, can we talk about this hoosier cabinet? It has a storage bin for flour and a sifter built right in! I didn’t roll out my piecrust on it but it was perfect for photographing the pie. (I also learned that it is called a hoosier cabinet – I had no idea).
Some other highlights included:
A visit to the Vermont Country Store.
OMG this place was fantastic – packed full of everything… and I do mean everything! We wandered through every corner of the stairs (upstairs and downstairs and even through the discount tent which was full of old waitress uniforms and broken Christmas ornaments, among other things). I tested cheese, played the spoons and tried on masks. I love an opportunity to just explore and goof off for awhile.
A trip to their friends/neighbors’ farm.
It has been ages since I’ve been to a farm, and this part of the trip was a real eye-opener for me. When we arrived Jo & Gus noticed that the turkeys were getting out – like 100 of them. It looked like a scene right out of chicken run – seeing all these turkeys sort of wandering/sneaking out, en masse, on the side of the barn. This probably should not have been funny to me, but witnessing this escape attempt, and then Gus and the owner trying to wrangle them all back into their pen, was relatively entertaining. I only wish I had a video to share.
The neighbors also raise chickens, both for eggs and for meat. So not only did I get to see all of the chickens of various ages (they seemed happy but OMG the smell), but I also got a full tour of their processing facility (just a tour, not a demo). I have to admit that it changed my opinion on consuming chicken ever so slightly and impressed upon me the importance of small farms and locally raised chickens that are treated humanely. But also at the same time the thought crossed my mind that maybe I could and should not ever eat chicken again! I will spare you the details.
Lots and lots of photo opps.
I had hoped the leaves would be turning, and they were, just a little bit. But Vermont is so charming and photogenic! So everywhere we went the conversation went like this:
Me: Oh my gosh that’s so cool! (or cute, or charming, or whatever)
Jo: Do you want me to pull over? (or turnaround)
Me: Do you mind? I actually wore myself out using that phrase. Of course she never minded.
On our way to pick up lunch one day I think we stopped like 10 times. I was STARVING. But I couldn’t resist a chance to take some photos. I think I ended up with a pretty cool collection.
One of the craziest things that happened was when we were having lunch in Brattleboro.

We had just sat down and I went to use the restroom. When I walked out to head back to our table there were 2 ladies coming into the restaurant. I hadn’t really noticed them yet when one of them declared to me “I know you!” I looked at her as she asked, “where do I know you from?”
From Italy.

Yep, I had run into her (Amy) and her friend Andrea on their last day in Riomaggiore just this summer. We were staying at the same hotel and they started chatting with me at breakfast and I ended up joining them and talking for quite some time. We became friends on Facebook. I had mentioned that I would be coming up to Vermont in October and they told me to reach out but I didn’t as I figured it would be nearly impossible for us to meet up as I couldn’t remember where they lived and I wouldn’t have a car. Well, the universe took care of that for us! People say all the time that it’s a small world and that’s really all I could think of this impromptu reconnection.
It was a truly a wonderful weekend and I was a bit sad when it had to end. But I’ll be back. And besides, I had other places to get to!
Part 2: Maine
I decided since I was already up in New England, and my flight had been paid for, that I might as well visit Maine! So I did (37 states now visited). I had two nights, but just 1 ½ days there. I wish I’d booked more time, not just to be in the city but also to explore Maine a little more. But I will go back. It’s not going anywhere.
To get to Portland it’s a relatively short drive from Boston – it took me just under 2 hours! I had hoped for a couple of things during this trip that just didn’t happen. 1) I thought maybe because it’s so far north that the leaves would be further along (they were not, although I still saw some beautiful trees) and 2) I wanted some fall weather! It was 80 both days, and I was not prepared with what I had packed so I literally sweated it out the entire time. Although the evenings were quite pleasant.
So, my main Maine goal was to eat my way through Portland. It has been called one of the foodiest small cities in America so yeah, trying as much local fare as possible seemed like a reasonable life goal.
And eat, I did.
But before I get to that, I want to tell you how much I loved Portland. Like, so much that I could imagine myself living there (maybe not in winter though?) It is charming (there’s that word again). Lots of cool architecture and outdoor spaces. And of course it’s also on the water. For those who live in Kansas City you will understand this analogy – if you took the crossroads district and made it into its own city – that’s what Portland feels like. It was fairly easy to get around via car or walking. Also there’s lots of biking. There are museums and shops and restaurants and all the things that make a town both visitable (is that a word?) and livable. And loveable (also not sure if this is a real word).
I had a day and a half there, which I know now was definitely not enough time. I like to explore on foot, so after having breakfast I wandered around for awhile until I reached the piers. I was hoping there would be a place to walk out and see what the fishermen were bringing in, but I never could quite figure out where that would be. So I browsed a couple shops and noticed that for a Tuesday morning it seemed really busy in the downtown. I soon learned that a cruise ship had come in.
It was hot – and I wanted to explore this little island area, so my plan was to change into something that could handle the heat better (leggings instead of jeans), grab lunch and then go explore Mackworth Island State Park. And all was going well until I got to the state park. And I couldn’t find parking. And there was a sign that politely stated that if you can’t find parking, come back another time. Well, ok then.
I drove back into Portland (just 15 minutes) to the Eastern Promenade, which is an overlook and walking path along the water. And while it wasn’t what I was hoping for, the view of the water was quite lovely and I felt like I was getting a little fill of nature, which is what I wanted.
I then ventured back into downtown in search of ice cream. I found it, and then went to this little park to eat it (but it was almost melting too fast for me to keep up!) I checked out a few other shops and then ventured back to my hotel for a break before dinner.
My second day there I had a few hours to explore before heading back to Boston to catch my flight, and since Maine is famous for lighthouses, that was what was on my agenda.
I first stopped at Bug Light Park to see the lighthouse there. It was little and so cute! And there was a good view back to the Portland skyline which was pretty cool. But the main (Maine) attraction, and more famous lighthouse, is the Portland Head Lighthouse. There is a large park near this lighthouse, and there were tour buses and quite a few visitors here. But it was worth it. It’s beautiful and I was able to get a few nice photos. I’m not really a nautical photo type of gal, like I won’t hang these on my living room wall, but it was still cool to capture this part of the adventure.
I attempted a third lighthouse but Google steered my wrong, and I ended up at a state park which stated very clearly that you could not see the lighthouses there… so it was a bust and it was time for me to head to the airport.
Ok, now back to the food.
I did some extensive research and also received some recommendations from a friend who used to live there. But there definitely was not enough time (nor stomach capacity) for me to eat everything I wanted to. I’d say I made a pretty good go of it though.
Of course Portland is known for Seafood. Like, really fresh, probably caught within the last 24 hours, seafood. But it’s really an up and coming food city with lots of delicious non-seafood options too.
I realize that this post has gotten really long – so, if you want to know more about what I ate and the places I’d recommend, check out this post on where and what I ate in Portland!