A Weekend Guide to Portland, Maine

Portland, Maine is one of New England’s best-kept secrets. The quaint Maine city is slowly growing in popularity, but it still feels like very few people realize just how special Portland really is. Growing up in New England, then attending college in central Maine, I have visited the coastal city of Portland more times than I can count. To help you plan your own trip, here is my ultimate weekend guide to Portland, Maine!

Portland, Maine

The food scene is unrivaled, as is the beer scene – there are amazing breweries everywhere. If you’re new to my blog (welcome), you’ll soon learn that I’m also obsessed with coffee shops. Portland, Maine has some of the best coffee shops in the entire country. Whether visiting Portland for the weekend or for the week, you will never run out of fun things to do.

How to Get to Portland, Maine

Despite Maine’s location in the very far northeast of the United States, it’s actually fairly easy to get to.

You can fly directly into Portland’s airport, Portland International Jetport (PWM), located just two miles from Portland’s downtown. If you have the budget, it’s worth paying a little more to fly directly into Portland.

Drive from Boston to Portland

Unfortunately, most flights into Portland’s airport are too expensive for travelers. Fortunately, though, Portland is just under two hours from Boston (1 hr 45 with no traffic!). Regardless of whether or not you fly into Boston Logan International Airport (BOS) or Portland (PWM), you will need to rent a car as public transportation is limited in Portland. That said, you can simply book a much cheaper flight into Boston then rent a car to drive the two hours north.

If you drive from Boston, check out Portsmouth, New Hampshire; it’s such a cute little city! I frequently stop at The Juicery for an acai bowl.

If you would prefer not to rent a car, or want to wait until you reach Portland to rent a car, there are other easy modes of transport. Amtrak and Concord Coach Lines both serve the Boston to Portland route with frequent daily departures. Portland does have Ubers so that is always an option, as well.

The Best Time to Visit Portland, Maine

When is the best time to visit Portland, Maine? It depends (I’m pretty sure that’s the answer to all “when is the best time to visit…” questions). Seriously, though, it really depends on several factors:

Do you want to be able to sit outside at the breweries and walk around without a jacket? Then stick to the summer months. Even May can be cold so aim for June-August.

Street in Portland Maine that is closed off from cars. There is a white sign that reads bikes and peds only. On the street there are flowers, trees along a brick sidewalk, and outdoor picnic table dining with a white tent.

Can you tolerate the cold? Since I grew up in New England and spent four years living in Maine, I am able to (sort of) handle the harsh weather. If you can bundle up, Portland in the off-season can be magical. Labor Day in September to Memorial Day in May (excluding holidays/school vacations) is considered off-season in Portland. There are fewer tourists so you can explore Portland without fear of restaurant wait times, waves of bachelor/bachelorette parties, and claustrophobia in the small boutique shops. It’s also easier to park along the street. Hotels are much cheaper in the off-season, as well (think $300 off normal nightly rate).

If you like snow, you should try to visit in the middle of the winter. Maine gets a lot of snow but with Portland on the coast, the weather is a bit unpredictable. Sometimes it snows a ton and sometimes not at all – but if you do see snowfall in Portland it is so pretty!

If you want to experience the fall foliage in New England, try to visit in mid-September through October. While living in Tennessee, I didn’t realize how much I would miss the leaves changing color. Sure, the leaves change in Tennessee, but it happens very quickly and it’s nothing compared to New England.

Where to Stay in Portland, Maine

Old Port, Portland, Maine with cobblestone streets, brick sidewalks, and brick buildings. There is a sign hanging on the right that reads Old Port Tavern. — Old Port in Portland

A weekend guide to Portland, Maine would not be complete without a place to stay. While there are several neighborhoods in Portland, downtown is the best area to stay. Areas outside of downtown will still remain accessible with a rental car, but you can relax knowing that pretty much everything is within walking distance should you stay downtown.

Downtown Portland consists of several notable neighborhoods, including Old Port, the Arts District, West End, and East End. Old Port is where you will likely spend the majority of your time. The Old Port, located along the waterfront, is filled with restaurants, bars, shops, and even a few breweries.

Best Portland Hotels

Depending on the time of year, hotel prices in Portland fluctuate quite a bit. In the winter, luxury hotels can fall in the low $100s before skyrocketing back up as high as $500+ for a single night. If you have a chance, book a stay at my top hotel recommendation: The Press Hotel.

Exterior building of Press Hotel. There is a sign the says Press Hotel. — **The Press Hotel** – 119 Exchange Street

Featured in many popular publications, like Architectural Digest and Travel + Leisure, The Press Hotel is a boutique, historic hotel in the Old Port. Voted #6 in Top 50 Hotels in New England in 2019 by Condé Nast Traveler, this hotel is one of Portland’s best places to stay. The Press Hotel is famously located in what was once the home of the Portland Press Herald, Maine’s largest newspaper.

More great options in Portland, Maine include:

Airbnb in Portland

If living like a local is more your style, Airbnb’s are on the rise in Portland. From cozy downtown lofts to historic Victorian homes, Airbnb offers visitors an array of options to fit your aesthetic and functional needs.

If you have never used Airbnb before, here is a link so you can save $50 off your first booking. My link will also provide you with a $15 credit to try out Airbnb experiences.

Best Restaurants in Portland, Maine

exterior of Flatbread Company pizza restaurant in Portland Maine. There is a boardwalk that surrounds the building that is waterfront. In the harbor there are a few large boats. — Entrance to Flatbread Company – 72 Commercial Street

Portland is heaven for foodies. A quick Google search will reveal just how many incredible restaurants there are. It can be a little overwhelming, especially if you only have a few days in the city. I advise starting with my personal favorite restaurants (so far):

Portland Coffee Shops Not to Miss

My favorite coffee shop in Portland, Maine is Coffee Me Up. A family-owned business run by a husband and wife, Coffee Me Up stands out in a city impressively saturated with top-rated coffee shops. Unlike most specialty coffeehouses, Coffee Me Up has a wide menu of European and American options as well as a range of cup sizes. Bard Coffee, another fantastic coffeehouse, serves great coffee, but lattes are consumed in half a second because of the limited size.

Exterior of Coffee Me Up coffee shop in Portland, Maine. There is a table in front of the entrance due to COVID-19. — Coffee Me Up – 221 Cumberland Ave

Another reason why I love Coffee Me Up, aside from the rich espresso and balanced Arabica coffee, is the food. The homemade bakery, breakfast, and lunch menu selections are delicious. Lastly, the staff at Coffee Me Up are always so friendly and I really appreciate the warm atmosphere the team works hard to inspire.

In addition to Coffee Me Up, other Portland coffee shops worth visiting include:

Tandem Coffee Roasters
Speckled Ax
Bard Coffee (small cup sizes but tasty coffee!)
Navis Café (awesome food menu)

Tandem Coffee Roasters – 122 Anderson Street Location

Best Portland Breweries for Local Beer

While technically not a brewery, I need to put a little plug for one of my favorite little bars in Portland, Maine: Tomaso’s Canteen. If you have time to stop by this welcoming neighborhood bar and grill, definitely add it to your Portland to-do list if you want to sample a collection of local crafts.

Now, onto the best Portland breweries for local beer. The Portland brewery scene invites an adventure unlike any other. From revitalized industrial buildings to downtown city hangouts, the breweries in Portland collectively champion authentic Maine experiences elevated by local craft beer. I put together a Google Map to help you plan your outing, whether it be a single stop or a multi-brewery excursion. Cheers!