My partner and I took a road trip across the Northeast Coast, and our first stop was Portland, Maine.  While we only spent a day and a half there, we were able to pack a lot during that time and enjoy the beauties of the coast.  If you’re passing by and only have limited time, this itinerary might help you pin-point what it is you want to do.

Lodging:  Hyatt Place Portland – Old Port

Neighborhood: Old Port – it’s filled with so much charm and plenty of restaurants/things to do.

Summary

Day 1:

• Kennebunkport
• Cape Elizabeth
• Dinner – Thirsty Pig

Day 2:

• Breakfast – Holy Donut
• Morning walk from Old Porte to Eastern Promenade
• Allagash Brewing Company
• Lobster Shack
• Two Lights State Park
• Dinner – Duckfat
• Nightcap – Bar of Chocolate

If you have time…

• Desert of Maine
• L.L. Bean Boot

If you’d like to see a full itinerary of our road trip, check out Road Trip Across the Northeast.

Day 1: Explore the Shore

We drove 5.5 hours from the NYC area straight to Portland.  If you haven’t been to Boston, you can add it as part of your itinerary since it’s not too out of the way.  Because we’ve already visited Boston, we decided against it and went straight to our destination.  We could tell we were getting closer to the Portland area once we started passing through some very cute towns and finally saw a glimpse of the Atlantic Ocean. 

Kennebunkport

The road led us straight through the Kennebunkport downtown area, which was very crowded.  Because we were taking COVID precautions, we decided to skip the downtown area and instead took a turn somewhere that led us to St. Ann’s by-the-Sea Episcopal Church, a beautiful church next to the shore.  We snapped a few pictures, took a seat at one of the benches, and finally relaxed for a bit after the long drive.  Not too far from there was the Goose Rocks Beach (about a 5-minute drive), which was a very intimate beach right in front of a cute hotel called Tides Beach Club.  We were only there for about five minutes since we were not dressed for swimming, but it was enough to dip my toes in the warm and clear water. 

Cape Elizabeth

We made our way to the Portland Head Light in Cape Elizabeth, which has the oldest lighthouse in Maine (completed in 1791).  In addition to its historical significance, it also has stunning views, walking paths, playgrounds, and beach areas to explore. 

Dinner in Portland

We finally made our way back to Portland, where we stayed at Hyatt Place Portland – Old Port, located right in Old Port, a charming historic district with brick buildings and cobblestone lining the streets.  It’s centrally located to popular restaurants, one of them being the Thirsty Pig, which was a casual spot that offered house made sausages and craft brews. 

Day 2: Portland, Beer, and Lobster Rolls

Breakfast and Morning Walk

Before starting the day, we stopped at the Holy Donut to grab some delicious donuts – which by the way are made from potatoes (you wouldn’t even know)! I think we had the Triple Berry Glaze and an Old Fashioned.  We did a full loop walk around Portland, starting from Old Porte to the Eastern Promenade and then through the backstreets of Portland — where we ended back at the hotel.  If walking isn’t your thing, you can definitely rent some bikes as well!

Allagash Brewing Company

The Allagash Brewing Company is a popular beer founded in Portland, so we thought we’d visit it and relax there for a bit.  Unfortunately, because of COVID restrictions they were not offering any tours or indoor/outdoor seating.  So, all we were able to do was pick up some of their select beer and take it back with us.  Thankfully, our next stop had even better views to drink a cold beer in. 

Lobster Rolls Near the Shore

The Lobster Shack is located at the end of Two Lights Road on the rocky shores of Cape Elizabeth.  It has picnic tables where you can enjoy a delicious lobster roll next to a beautiful view.  Instead of sitting in the picnic tables, where it didn’t allow any outside food/drinks (we had beers), we veered off to a left trail right next to the shack, where it led us straight down to the shore and where there were plenty of rocks to lay/sit on.  My partner enjoyed his beer, and I enjoyed my lobster roll, then we laid on the rocks for maybe 45 minutes – which by the way, were very comfortable. 

Two Lights State Park

If you’re willing to pay a few bucks and want a little more privacy, you can also head to the Two Lights State Park.  When we went, it was absolutely lonely, and we had most of the place to ourselves. 

Dinner and Dessert

Duckfat is known for its delicious Belgian fries that are fried in, surprise, duck fat. I had been eyeing them for a few weeks, so I’m very excited to say it didn’t disappoint. After dinner, we ended our final night by doing a nightcap at Bar of Chocolate, which had delicious alcoholic drinks as well as desserts. 

If you Have Time…

Desert of Maine and L.L. Bean Boot

On the third day, as we were heading to Acadia National Park, we made a quick stop at the Desert of Maine.  I’ll be honest, I don’t know if I would’ve gone out of the way if I wasn’t already passing by, but if you’re up for weird and quirky, then go for it!  The Desert of Maine is filled with sand dunes and has an interesting history.  It cost $10 per person to enter, which gives you access to walk the dunes and surrounded along the perimeter are some historic facts that you can read.  It only took about 25-30 minutes to walk the entire dunes, and then we were on our way to Freeport, which is known to be L.L. Bean’s original flagship store. Most importantly, it has the giant L.L. Bean boot!  After taking a few pictures, you can explore the flagship store and grab some coffee at the 1912 Café. 

There are plenty of things to do around Portland, that unfortunately we didn’t get to in the one and a half days we spent there – but nonetheless, our itinerary was packed and productive.  If there is one thing I would have added, it might be taking the ferry to the Casco Bay Islands.  If you’re heading to Acadia National Park/Bar Harbor, don’t forget to check out our post Top Things to Do in Acadia National Park.