Maine - Portland
September 2020
3 Days
With COVID restrictions still in full swing and getting a bit stir crazy, we planned an East Coast road trip with another couple. I had never been to Maine, so we made Portland, the biggest city in Maine, our first stop. We considered taking a day to visit Acadia National Park but after the 16 hour drive from Chicago nobody was really up for another 3 hour drive. We still had a great time exporing Portland and eating a ton of fresh seafood.
Contents
Daily Itinerary
Start the day with breakfast at Becky's diner
Explore the Old Port area
Walk down to the docks
Order some fresh seafood to take home
Oysters on the water at J's Oyster
Sail around the bay with Portland Schooner Co
More seafood for dinner at Eventide
Try Portland's most famous donuts at the Holy Donut
Drive to Freeport to shop 'til you drop
Grab roadside lobster at Day's
Take in one of Portland's most iconic scenes at the Portland Head Light
Drinks and dinner on Wharf Street
Begin the drive South along the coast to Cape Cod
Stop in the picturesque town of Portsmouth and grab lunch along the water
Flights
We drove the whole way there in one day although would recommend splitting it in 2 days. We barely did any driving as our friends were kind enough to do most of it!
Hotels
Hyatt Place Portland Old Port: 2 free night certificates
▸ A standard Hyatt Place centrally located to all the tourist attractions and restaurants in the Old Port
Canopy by Hilton Portland Waterfront: 1 free night certificate
▸ Modern hotel centrally located right on Commercial Street with a rooftop bar overlooking the water
Food (With Beli Ranking)
Eventide Oyster Co. (9.3) - Delicious restaurant with a raw bar and some of the most delicious clams. Famous for the brown butter lobster roll which is a must try.
Day's Crabmeat & Lobster (8.5) - Small roadside shop open seasonally for takeout or you can eat at the tables outside. Probably the freshest tasting lobster we had on our trip.
J's Oyster (7.9) - Small restaurant on one of the piers serving oysters, clams, lobsters, and tons of other fresh seafood.
Becky's Diner (7.4) - Simple diner right near the docks serving great breakfast, lunch, and dinner. Usual diner staples on the menu plus fresh seafood.
The Holy Donut - Famous for their sweet potato donuts, there was always a line when we went past but the wait was worth it for these delicious donuts.
Full Itinerary
Day 1
After arriving in Portland late at night following our 16-hour drive, we started the first day with a solid breakfast. Becky's diner is highly rated and did not disappoint. They have a very standard diner breakfast menu, but the homemade corned beef hash was to die for! There's also plenty of lobster included in the breakfast options too.
Becky's Diner - Portland, Maine 2020
Commercial Street
Walking north on Commercial Street from Becky's Diner, you'll soon be on the main section through the Old Port. On one side are the docks with several seaside seafood restaurants. On the other side are the narrow cobblestone streets of the Old Port, lined with shops and restaurants.
Docks off Commercial Street - Portland, Maine 2020
Harbor Fish Market
Located right on the water, if you are looking for some fresh seafood to take home, you'll want to stop by the Harbor Fish Market. If you're not a local, you can have live lobsters and other seafood delivered overnight to your home at any time.
Harbor Fish Market - Portland, Maine 2020
After a morning of exploring the Old Port, it was time to get some fresh Oysters, so we stopped by J's Oyster to get a dozen or two.
J's Oyster - Portland, Maine 2020
Portland Schooner Co
In the afternoon of our first day, we booked a cruise around the bay with the Portland Schooner Company. You can bring your own snacks and drinks on the ride, so even though it got a bit chilly, it was a perfect way to spend the afternoon.
Portland Schooner Co - Portland, Maine 2020
Eventide Oyster Co. was recommended to us by several different people, most notably known for their oysters of course. Since we had oysters for lunch, we tried some other items on the menu and they were absolutely amazing. The lobster stew has to be one of the best soups I've ever had. And the famed brown butter lobster roll also lived up to the hype.
Eventide Oyster Co. - Portland, Maine 2020
Day 2
During day 1 walking around the Old Port we ran into The Holy Donut shop with a line down the block. We had planned to drive to Freeport, so we stopped at a different location on the way out of Portland. Their claim to fame is that some of the featured donuts are made from sweet potatoes. The line was worth the wait because they were absolutely delicious!
The Holy Donut - Portland, Maine 2020
Freeport
Freeport is a small town just 20 minutes from Portland known mainly for its shopping outlets, restaurants, and as the headquarters of LL Bean. There’s a number of other name-brand outlet stores, which kept us busy for the morning.
Freeport, Maine 2020
After a morning of shopping, we (mainly me) were on a mission to get roadside lobster. Just off the highway, between Portland and Freeport, we stopped at Day's Crabmeat and Lobster, a small roadside stand with a large outdoor seating space out back overlooking marshland.
As with all of our lobsters this trip, Day's did not disappoint. The full lobster, lobster roll, and clam chowder were all exceptional.
Day's Crabmeat & Lobster - Yarmouth, Maine 2020
Portland Head Light
When you think of Maine, the Portland Head Light is probably the first image that pops into your head, even if you didn't know that's what it's called (I definitely didn't). Just a 15-minute drive outside Portland, it's worth a quick stop. There's a walking path along the coast although we didn't go too far since the weather was not great. Good thing we bought some new warm clothes in Freeport!
Portland Head Light - Cape Elizabeth, Maine 2015
Wharf Street
Wharf Street, in the Old Port, is a brick walking street lined with restaurants and bars, and a great place to spend an evening. Via Vecchia is pictured on the left, although we had dinner at Central Provisions which was recommended to us by several different people. The Asian inspired food and tropical drinks helped us forget that it was only about 50 degrees outside while we were eating.
Wharf Street - Portland, Maine 2020
Day 3
Portsmouth, NH
The second half of our trip was in Cape Cod and our schooner captain recommended that we stop in Portsmouth, New Hampshire, about an hour south of Portland. Portsmouth was a great place to stop and spend a few hours perusing the small shops and viewing the preserved Colonial era buildings. It would also be a great day trip from either Portland or Boston. There are a number of restaurants along the water where we stopped to eat lunch before continuing on to Cape Cod.
Portsmouth, New Hampshire 2020
Overall
We planned our trip to spend 2 days in Portland and 3 days in Cape Cod, although I would love to return to Maine and spend much more time in the state. 2 full days in Portland was a good amount of time to stay and get my fill of seafood. Next trip, I would plan to drive further North up along the coast. We considered trying to visit Acadia National Park this trip (we did end up visiting in 2025), but with a 3 hour drive each way we just didn't want to spend that much more time in the car (especially after driving 16 hours in one day to get there!)
To see the next stop on this trip, go here to Cape Cod
