Greetings from, Maine! Well, virtual greetings 😆 We took a trip to the northeast back in September with Cliff House Resort in Cape Neddick, ME as our anchor destination! It was such a beautiful and memorable vacation with our then 10 month old that we will never forget. So buckle up friends and let’s take a vacay!

P.S. see tips I’ve shared for traveling with a baby here and here.

Traveling somewhere soon? We have an interactive travel map sharing where we’ve gone and the best things to do there!

Let’s talk logistics…

Where did we fly in?

We flew in to Boston Logan International Airport [which is about 1.5-2 hours from Cliff House]. If you would like a closer airport you could fly into Portland, ME [less than 1 hour from Cliff House].

Did we rent a car?

Yes! We rented a car and picked it up at the airport. We also rented a carseat from the rental car company which I definitely recommend for ease of traveling and less lugging of baby gear!

What was the weather like?

We went in the middle of September [which is the middle of hurricane season, and unfortunately we were in the line of Hurricane Lee. Thankfully, we were all okay!]. Other than it being rainy quite a bit of our trip, it was beautiful and in the 70s!

Day 1 + 2: Winthrop, MA / Boston, MA

We stayed in Winthrop [about 15 minutes from downtown Boston] at the CUTEST little airbnb! It was a great price and location.

We decided to do carry out for dinner our first night after a long day of traveling and grabbed food from Nick’s Place [I got a gyro bowl and it was super good and filling!].

The next morning walked to deer park for a morning stroll [and watched the airplanes take off over the bay along the way] then made our way downtown Boston to explore! First stop was Boston Public Market [pro tip: you get 3 hours of free parking in the Parcel 7 parking garage with Public Market validation! I would take advantage of this because parking can get pricey in Boston]. I grabbed a cup of clam chowder in the market at Red’s Best and a very yummy sweet treat at Jennifer Lee’s Allergen friendly vegan bake shop! We had to stop in at America’s Oldest Tavern, Bell In Hand which is located in the heart of Government Center, next to Faneuil Hall Marketplace!

My husband loves a good college campus visit, so we drove through Boston College and Harvard. It was rainy pretty much all day, so we stopped in at The Druid [a cozy Irish pub in Cambridge] and grabbed a pizza from Pinocchios Pizza [a Harvard staple] to take back to our Airbnb for a night in and football.

Day 3: Rockport, MA

Rockport, MA is a dreamy little town 40 miles north of Boston! Whether you want to stroll the shops, galleries, and restaurants of Bearskin Neck or enjoy the sights of bay, Rockport has so much history to take in and feels like it’s plucked out of a novel.

From following along Erin’s 8 days in the Northeast post, we had to stop at Roy Moore Seafood Shack. It was super cute, quaint, and located right in the heart of Bearskin Neck. Be sure to stop to see the Motif! While it won’t take long, it is known as one of the most painted and photographed buildings in the world.

After our stop in Rockport, we ventured on to Cliff House…with another stop along the way of course! We stopped at Great Rhythm Brewing in Portsmouth, NH [spoiler alert, we’ll be back at Portsmouth later in our journey] for a pint [loved the Octoberfest! 🎃].

Day 3 + 4 + 5 Maine [Cape Neddick, Ogunquit, Kennebunkport]

WE ARRIVED AT CLIFF HOUSE! If you don’t follow their Instagram account I love to look at their posts and day dream about cozying up in the hot tub looking over the cliffs. The views are SO beautiful here – it’s breathtaking!

After checking into our room, we ventured out and had dinner at yet another lobstah [gotta say it like this] shack Foot Bridge Lobster [hi, I love good seafood]! It is so cute and cozy inside and the food was A+!

The next day we soaked up the amazing views in the Cliff House lobby while sipping coffee and I could’ve just sat there all day! We booked massages [separate times because of switching off for baby duty] and the “Seaside Sanctuary” that you can sit in before and after your massage is a little slice of heaven. The spa amenities in the resort overall are great.

I highly recommend walking along marginal way. It’s 1.25 miles one way and the views are incredible! After our walk we went to Oarweed for lunch and 10/10 would suggest for a yummy lunch with great prices and an amazing view!

Other noteworthy places to eat: Cape Pier Chowder House [this one is definitely more off the beaten path!], Féile Irish Pub, and the dining experiences at Cliff House!

Day 6: Portsmouth, NH & Salem, MA

We stopped back in Portsmouth, NH on our way from Maine to Boston to really stroll and take it all in this time. Here are some favs I recommend trying if you find yourself in this super cute and beautiful town!

• Stoneface Brewing [the burger is 💯]
• Red Rover Creamery [amazing handmade ice cream 🤤]
• Hearth Market [beautiful food hall and shopping!]

There’s so much history surrounding Salem, MA and I wanted to make the stop while we were close by! Here’s what we did during our quick, but fun little tour of Salem:

• Walked Chestnut Street [often labeled the most beautiful street in America for its architecture!]
• Walked by the Witch House [this is one of the few structures you can visit in Salem with direct ties to the Salem witch trials of 1692].
• Visited the Salem Common and Derby Waterfront
• Last but not least, we had to snap a picture with the Bewitched statue [as shown above] 🪄 because I loved that show as a kid!

Day 7: Boston, MA

Alrighty, we are back to Boston y’all! This time we just stayed in a hotel near the airport since we were flying out the next morning.

We wanted to try to soak up the history of the city and walked the freedom trail! You can do guided tours for this, but we opted to just walk it on our own and read along the way. From Paul Revere’s house, to Granary Burying Ground, to King’s Chapel, to Boston Common – this trail has so many historic markers of the American revolution!

While exploring the freedom trail we stopped to grab a super yummy lunch at Trattoria Il Panino in Boston’s north end. [The portions are huge!] I also had to go full tourist and try some cannoli’s at Mike’s Pastry [this line was LONG but it was a fun experience!]. Now, as amazing as this food was one of the biggest surprise highlights for my tastebuds was a roast beef sandwich at Billy’s Roast Beef & Seafood. You need to try this place!

And just like that, we were off [after some flight maneuvering due to weather] back to Indiana! Cheers to a great trip with amazing memories. If you head this way, let me know what you loved! xoxo Katy

What I Packed: