We recently wrapped up an amazing trip to the east coast with our two year old (vacation vid here!) so I wanted to share my recommendations for any other fellow leaf peepers out there (although all recs still apply in non-snowy months). I’m going to split this into two posts, one covering the Portland Maine area and the second focusing on Stowe and Woodstock.

We first visited Portland three years ago when I had just found out I was pregnant and we hit many of the destinations below way back in those innocent, pre-parenthood days of 2016 so they definitely stand the test of time.

The big decision is to figure out where you want to fly into - we chose to fly into Boston and rent a car. This option proved considerably less expensive with a much-preferred nonstop flight and all we had to do was embark on a very pleasant early evening drive versus a super long day with a (potentially disastrous) layover. I’ll do a layover if I have to do but if it at all makes sense to skip it I definitely will. Once you make it to Portland, here are our top recommendations:

Food:

Eventide - this is probably one of the most popular restaurants downtown and there is a clear reason why. It’s usually packed with a long wait but one of the few benefits of traveling with a youngster is you usually eat dinner on the early side and can avoid the most populated feeding times (I kid, there are many wonderful things about traveling with kids!). Just order everything on the menu and thank me later. But if you’re looking for some specific must-try items, I’d do the lobster roll, fried oyster roll, the crudo and the lobster stew. We ate outside and I found it to be very kid friendly for a long leisurely lunch.

Duckfat - this savory hot spot is slightly less kid friendly, mostly because some of the tables are communal, but still totally worth it! The food is decadent and delicious and the milkshakes (some made with the titular duck fat) are out of this world. This is another destination that’s super popular and often requires a bit of a wait.

The Holy Donut - go here and order many dozens of donuts! From chocotastic dark chocolate sea salt to a zesty Fresh Lemon and they’re made out of potatoes. Potatoes!!! They’re delicious and they even have gluten free options.

Miyake - this is not a kid friendly restaurant per se (they don’t have high chars) and it’s obvious that not many people are rushing to bring their kids here, but if you’re looking for delicious Japanese food (from a stunning multi-course Chef's Omakase tasting menu to one of the best crab cakes I've ever tasted) and you’re kid is pretty content at restaurants, this is a really great option.

Do:

Lighthouse and lobster rolls in Fort Williams Park - can you go to Maine without at least one visit to a lighthouse? I don’t think it’s possible. This is a short drive from Portland and is beautiful, easily accessible (don’t worry about parking far away and having to hike in) and most conveniently for food-crazed vacationers after you explore for a while you can stop and have a delicious lunch from the Bite Into Maine lobster roll truck. I highly recommend ordering the XL lobster rolls because I guarantee you’ll finish the regular size too fast and wish you’d ordered another one. Delectable!

Deering Oaks Park - we found this awesome playground on our last day and wish we’d discovered earlier. It’s tucked away in the middle of Deering Park with easy parking and a slide that takes you down into the park (which I think is a great way to get kids and adults into a playful mindset!). There’s a huge climbing net for older kids, two playgrounds based on age, some swings and other various items to play with. I also loved the general design of the park. Unlike most parks that are bright green and red this one really blended into the surroundings and felt like you were playing amongst the trees in a one-of-a-kind environment. Bonus points for tree trimming going on while we were there so our toddler got to excitedly watch a crew mulch trees.

Explore downtown and make a stop at Little and Treehouse Toys - downtown Portland is full of cute shops and is extremely walkable. Spend some time exploring the local coffee shops, books stores, clothing boutiques and make sure to stop in the one-two punch of toy store awesomeness with Little and Treehouse Toys. They are conveniently located across the street from one another and they each have unique selections. At Little you will find more upscale and boutique toy brands, Maileg and Candylab and high end clothing from Rylee + Cru. Treehouse has an excellently curated selection of toys from larger brands with very little overlap from next door. We usually pick up one or two small toys and a book on vacation. This trip we got a little stuffed mouse and bunny ear clips from Little and a special Fall-themed pumpkin book and stickers from Treehouse.

Children’s Museum + Theater of Maine - this is one of my favorite kids museums I’ve ever been to! It looks small but has dozens of amazing activities and displays covering three stories. There’s a huge play structure, an imagination area complete with a fire truck, car, fishing boat, farmers market, mini hospital and more. Upstairs there’s an amazing little river, a tide pool touch tank and LL Bean forest. For an added bonus go to the camera obscure upstairs or the little theater downstairs that has live shows and interactive programs. Also I can’t say enough about the amazing customer service. I totally forgot diapers (really not sure how I managed that!) and they stock all sizes in case of emergencies so they were able to help us out.

Stay:

We rented a pretty generic Airbnb this trip, but three years ago we stayed at the Press Hotel and it is to this day one of my favorite hotels ever. The rooms are beautiful and comfortable, the customer service is great and it’s perfect downtown location cannot be beat.

After our long weekend in Portland we took the scenic drive through New Hampshire to Stowe, Vermont. I’ll post my Stowe recs soon so stay tuned for that!

And If you have other suggestions please list them below in the comments or shoot us an email and we'll add it to our list.

- Callie