I’ve visited the beautiful state of Maine several times a year since I was young – maybe 8 or 9. My dad’s older sister and her family – my uncle and two younger cousins – live in Maine, so we’d go up there for long weekends numerous times every year. My aunt and uncle moved around a couple of times, but eventually settled a decade and a half ago, at least, in the small town of Freeport, just 45 minutes north of the state line.
Although I grew up with the singular intention of moving to New York City and I spent as much time as possible here, I eventually grew to like visiting Maine, too. At first my love for Freeport was cemented primarily because Freeport had an incredible outlet shopping scene and although I kind of hate shopping, I do love getting inexpensive basics from the Gap, which I definitely did every time we visited. (And some non basics. I definitely spent too much money there as a teenager, if we’re being honest.)
Now that I know the truth about fast fashion, I despise shopping even more and avoid it at all costs. Luckily, I’ve found other things to love about Maine, like the weather (yes, I love cold weather) and the food and Portland.
Where to Stay
More often than not, I stay at my aunt and uncle’s house a five-minute walk from the outlets in Freeport, but I’ve also stayed at the Hilton Garden Inn, as well as the White Cedar Inn Bed & Breakfast.
Hilton Garden Inn: This is your typical small-town Hilton. There are comfortable beds, clean white linens, free coffee, and more space than you could possibly need. There’s also a pool that is free to use for people staying there, which could be a nice respite from the frosty temperatures that Maine is known for in the winters. 5 Park St, Freeport, ME 04032, (207) 865-1433
White Cedar Inn Bed & Breakfast: I stayed here when one of my cousins got married almost three years ago. It was my first time staying in a B&B in Maine and it was definitely different from my prior experiences staying at the Hilton.
White Cedar Inn, Freeport, Maine
My family and I (+ one of my other cousins) arrived at the main house to check in on our first night there and we basically found ourselves in the living room and kitchen of the lovely people who operated the Inn. They gave us the keys and showed us the way to our rooms (back out the door, down the stairs, and in my building next door, to be precise).
The owners made breakfast each morning and there was always a pot of free coffee in the main house. I shared a room with my cousin and it was more than enough for a two night stay. There were towels and comfortable twin beds and a recently-renovated bathroom. It was a little different than what I’m used to because there was definitely no one awake all night to make sure no one broke in. It also wouldn’t have mattered if there was since our room’s entrance was outside and away from the main area’s door! But Freeport is a very safe place, so there were no issues. The breakfast was eggs, bacon, sausage, yogurt, etc. and it was very tasty.
If you’re someone who prefers to not have to see people when you come home from a day of exploring, this might be the spot for you. Honestly, I enjoyed the experience but I’m still not so sure how I felt about the main street being directly outside where I was sleeping. That’s just the city woman in me talking, I think. 178 Main St, Freeport, ME 04032, (207) 865-9099
Black Point Inn: I’ve never stayed in a hotel in Portland since my family lives so close but some quick Googling identified the Black Point Inn as one of Maine’s original waterfront luxury inns. While it’s not in the city of Portland, it’s just 7 miles outside of it. So if you’re looking for a view of the water, a geothermally heated pool, and a fitness center, this is your place. 510 Black Point Road, Scarborough, Maine 04074, (207) 883-2500
The Francis: This is one of Portland’s newest boutique hotels and it looks super cute online. It’s somewhat cheaper than the Black Point Inn. There are 15 rooms at the hotel and each one is different, which is kind of cool, too. 747 Congress St., Portland, Maine 04102, (207) 772-7485
Westin Portland Harborview: If you’re looking for your standard chain hotel, this is a good option. It’s cheaper than the other two and probably just as comfortable as every other Westin you’ve ever stayed in! 157 High St., Portland, Maine 04101, (207) 775-5411
What Towns to Visit & Eat:
I’m a little bit biased when I talk about where you should explore in Maine because I’ve only spent extensive time in two towns in the state. However, given that a lot of the state isn’t what I’d call a vacation destination if you like cities, I thought I’d be justified in concentrating on the following places:
Freeport: This adorable, progressive little town is home to the flagship location of the famous outdoor store, LL Bean. The shopping area has expanded in the last decade out from the main street and unfortunately more big fast fashion names like Old Navy are appearing but you can also still find independent jewelry and clothing stores if you wander down the tree-lined side streets. LL Bean’s campus is huge and you’d be blind if you missed it. It’s open 24 hours a day (in case you can’t get a reservation at a hotel!) and is composed of a half dozen or so buildings. There’s also a Starbucks near the campus as well as, of course, Ben & Jerry’s.
The LL Bean campus in Freeport, Maine
As far as eats, I’d recommend China Rose, the locally owned Azure Cafe, and the Maine Beer Company. The Maine Beer Company (525 US-1, Freeport, ME 04032) has pretty good pizza (this coming from a New Yorker) and it’s totally solar-paneled. They also brew several different types of their own beer! The Azure Cafe (123 Main St, Freeport, ME 04032) is a perfect spot for lunch or brunch, with its large windows that let in copious amounts of light and the simple wooden decor. It’s a perfect spot to support a local business and local food. China Rose (23 Main St, Freeport, ME 04032) is excellent Chinese food and it’s been operating for decades; and Mainers are pretty picky about their Chinese food I’ve learned!
Portland: I’ve spent less time in Portland but every time I’m there, I want to look into real estate prices and contemplate buying a summer home there (in my dreams!). I think that it’s the perfect blend of city life and smalltown life. There are plentiful sidewalks and you definitely don’t need to own a car to live within the city limits themselves, plus there are concert venues, theatres, and lots of restaurants.
Streets & Street Art, Portland, Maine
My cousin got married in a small concert venue called Empire Live Music & Events space located over the Empire Chinese Kitchen. I’d also been to a concert there (with her) several years back. It’s definitely an intimate and super cool space for a concert, event, or otherwise. Both the venue and the restaurant are located at 575 Congress St, Portland, ME 04101.
A photo from that concert at Empire Live Music & Events Space from the early 2010’s!
Here’s the space as a wedding venue in 2017!
During my most recent visit in January, Nick, my family, and me went to the Empire Chinese Kitchen downstairs and devoured all of the delicious food until our plates were clean. There were dumplings and rice and Kung Pao tofu and spring rolls and soup (and some non-vegetarian items for the meat eaters at the table!). I’d highly recommend hitting up this spot if you want some really good, hearty food to keep you warm (because it’ll likely be cold when you’re in Maine!).
Chocolate fortune cookies? Sign me up.
On this trip, we also stopped into The Holy Donut, a locally-owned donut shop that serves donuts that are piping hot right out of the fryer with glazes in flavors like pomegranate, or lemon, or just a simple sea salt is one of their most popular. If you need a little something extra, you can always pick up the Allan’s Coffee Brandy donut, which is glazed with a boozy coffee liqueur frosting. (The Holy Donut is located at 7 Exchange St, Portland, ME 04101.)
The Holy Donut in Portland, Maine
Lastly, I’d insist that you pick up dessert at the locally-owned Standard Baking Company. My aunt gave me their cookbook years ago and although I’m not hugely into baking (it takes too much precision, IMO), I always make sure to stop into their shop when I’m in town and at least pick up a chocolate chip cookie. (Located at 75 Commercial St, Portland, ME 04101.)
Bonus: Bangor: This is a bonus for horror movie / literary nerds everywhere. I’ve yet to venture another hour north up the coast to Bangor but I have friends who have made the pilgrimage just to see the sights that inspired certain locations in Stephen King’s books, like IT, for example. You can see not only Mr. King’s fabulous and slightly creepy home (which is being converted into a museum soon!), you can also grab a meal at the restaurant Oriental Jade (which served as inspiration for the infamous scene from the book IT) and there’s even a huge Paul Bunyan statue which you will also remember from IT. These are the things that I’d definitely be doing if I ever found myself with some extra time and a car in Maine!
There are multiple options for transportation up to Maine. If you live somewhere that requires a car, that is your best bet. It is by far the easiest way of traveling north in New England.
When traveling to Maine by public transportation, somehow I’ve always found that it takes a lot longer and it’s almost the same price as renting a car for the weekend. However, if you’re like me, and you hate to drive, you might opt for the few extra hours of travel time in exchange for being able to read a book and not having to scream at drivers in Massachusetts the whole way (because trust me, you will want to scream at them).
Bus: Unfortunately there are no direct buses from New York City to Maine. Companies like Greyhound, Bolt Bus, and Megabus run buses regularly from New York City to Boston and from there you can transfer to another bus that will take you to Portland.
Train: You can actually take a train all the way from New York City to Freeport, albeit there will be one point of transfer in Boston. During this stop in Boston, you’ll have to navigate your way from Back Bay to one of the other stations to board your connecting train. In addition, the train only runs to Freeport once (maybe twice) per day so if anything gets delayed on the first leg of your travels, you could miss your connection. I’d also be remiss to forget to mention that it’s a very expensive train ride.
Train + Bus: I’ve actually done this a couple of times. If I can book an Amtrak ticket early enough in advance, it winds up costing $50 to get from New York City to Boston and from there, a one-way ticket on the Concord Coach Lines is about $40. As I mentioned previously, there are buses to Portland with Greyhound and Megabus that are less expensive, but it might be worth the extra money to have a nicer ride on Concord.
You know that I’m not big into outdoor sports, but there are some pretty spots that you could enjoy without actually having to be in full hiking gear! Since it was the middle of January on my last trip to Maine, it snowed the night before we arrived so we went sledding. It was fun!
The sledding next to the Freeport Elementary School!
Popham Beach: My aunt and uncle were married here and although I was not at that wedding, I was at their recommitment ceremony a few years back. This sandy, three mile long beach is the site of the short-lived Popham Colony, founded in 1607 and abandoned the following year.
Portland Headlight: Just south of Portland, along the coast in a town called Cape Elizabeth, you’ll find a lookout point with a lighthouse that’s been in operation since 1791. You’ll be able to see several little islands that dot the Maine coast among the brightly colored buoys that apparently mark lobster catching. It was unbelievably cold when we visited in January, but it was worth it for the sunset.
We look happy, but we were freezing.
For a few extra ideas, I’ve enlisted the help of my Aunt Shari, a life coach and lawyer, because she lives there and she’s definitely into the outdoors:
Portland and its surrounding communities are home to many parks and preserves that are open to the public. Ranging from walking along the rocky coast to sandy beaches to quiet woods, rivers and ponds, there is a variety of outdoor experiences, including walks, hiking, bicycling, canoeing and kayaking.
Just south of Portland off Route 77 in Cape Elizabeth is Fort Williams Park, which features the remains of an old fort and one of the most photographed lighthouses in Maine sitting atop a rocky bluff. Continuing south on Route 77 are two pristine adjacent public beaches, Kettle Cove and Crescent Beach.
Off of Route 1 in Falmouth is Mackworth Island, connected to the mainland by a causeway. Mackworth has a 2 mile trail around the perimeter, and visitors can see a variety of sea and land birds, fairy houses in the woods and a panoramic view of Casco Bay.
Further north is Freeport which most people visit for the shopping. Here, there are many beautiful spots owned by the Freeport Conservation Trust, as well as Mast Landing Sanctuary and Wolfe’s Neck State Park, which has several miles of trails along the ocean and relatively close views of an osprey nest. If you venture to the South Freeport harbor Harraseeket Lobster offers fresh fried seafood, clams and lobster dinners.
If you’re not going to go camping in one of the surrounding parks or out to dinner at one of the locally-owned restaurants in Freeport, I’d strongly suggest hitting up Portland. I already talked about the Empire Live Music & Events Space and here you can check out their schedule here to take in the tunes of a small local band in a cozy space with a cheap drink. However, if tiny concerts aren’t you thing, these are a couple of other places you can visit after dinner in Portland:
Music: If you’re looking for a larger concert venue to maybe take in a performance by a more established musician, then head on over to the State Theatre. This is a larger concert venue where performers like Lyle Lovett and Tre Anastasio can be seen. While I was visiting my family back in 2013, I saw David Byrne and St. Vincent perform here! There’s not a bad seat in the house and all of the tickets are pretty affordable (remember, you’re not in New York City anymore!) 609 Congress St, Portland, ME 04101
Theatre: If the theatre is more your jam, check the schedule at the Merrill Auditorium (20 Myrtle St, Portland, ME 04101) and Portland Stage will be just the ticket (pun intended). At the Merrill Auditorium is where you’ll find national tours of Broadway shows. Head over to Portland Stage (25 Forest Ave, Portland, ME 04101) though and you’ll see more intimate productions with a more local cast of actors.
Breweries: If you’ve already sampled all of the beers on tap at the Maine Beer Company, then you’d be silly not to check out the Rising Tide Brewing Company in Portland, Maine, a small establishment that serves a variety of local brews with a plethora of outdoor seating. My cousin and her husband hosted their wedding weekend welcome happy hour here and it was a great warehouse-like venue with the most chill vibe you could’ve asked for. Rising Tide is located at 103 Fox St, Portland, ME 04101
And if you’re willing to drive a little bit further north of Portland, you’ll be able to check out the more nationally known Allagash Brewing Company that brews those delicious pale ales that me and so many others love. I have no yet had a chance to check them out, but I’d definitely like to someday. Allagash is located at 50 Industrial Way, Portland, ME 04103.
So that is everything you should need to have a perfect three days in Maine. Make sure to bring cuddly clothes to relax in front of a fire in at night, too. In the winter, snow boots are an absolute must too!
Have you been to Maine before? What are your favorite things to do there? I’m always looking for new suggestions! (Please no camping though!) xo – Allison