Winter Weekend in Portland Maine (eatcation)

What does a winter weekend in the pretty little city of Portland, Maine look like you ask? Well, it sort of looks like this: Fresh out of the oven donuts, french fries cooked in duckfat (and then smothered in gravy), delicious dumplings, more local breweries than you can possibly fit in a weekend, views of the sparkling Atlantic and yes, some snow.

Popular Summer Stop - Portland Lobster Co.

If you have lived in the northeast you can agree that New England winters seem to kind of drag on forever.  That fresh snowfall always gets us giddy, but by week 3 of sub freezing temperatures, icy bridges and dirty snowbanks mixed with garbage and gravel, we are beginning the countdown to daylight savings.  Sure, you can head to the mountains to ski but again, this is New England.  You can get a great powder day or a weekend filled with long lift lines, single digit temperatures and a lot (a lot) of ice.  So what do you do when the forecast is projected to be 20ish and the skiing conditions are awful?  You go on a Eatcation**. 

First official food stop on the way to Portland: Rise Donut from Congdons

* Eatcations can involve activities besides eating. However, the main reason for the trip and largest enjoyment must come from eating. For example: You can go for a nice little walk along the harbor, but you better be putting your all into Breakfast, Lunch and Dinner, with a stop at a brewery somewhere between there. The purpose: to eat some great food. Everything else is optional. Portland, Maine is just about the perfect place to go on a eatcation. Portland is Maine's largest city and has seen a dramatic transformation with the influx of foodies and hipsters that make this city what it is today. Bon Appétit named Portland America’s foodiest small town, the New York Times called Portland “one of the best places to eat in the Northeast,” and the current new title is in competition with San Francisco for the most restaurants per capita. 

In the summer, you have a lot more options as far as recreation goes from whale watching to walking tours. In the winter you are a little more limited. For this post, we are going to focus on what you can (and should) do during a winter weekend in Portland Maine. And like I said, this was an eatcation so I basically, well, ate.

Old cobblestone streets in Portland 

Portland has survived dramatic transformations and a few name changes.  From Casco (1633) to Falmouth (1658) to Portland (1786), it was a city with an identity crisis in it's early beginnings.   To go over some history, Portland's first home was built in 1632.  The British burned the city in 1775 when residents refused to surrender arms.  It was rebuilt and became a major trading center (it became a big port down due to its deep waters).  Much of Portland was destroyed again in the Great Fire of July 4, 1866.  Today, the harbor is filled with working boats, personal yachts and ferries.

Fancy condos and mini touristy cruise ships 

Old Port is the perfect place to walk through, any time of year.  In the winter, it is even a little more inviting with plenty of options for parking and less people crowding its streets.  Old Port is a major international port and a working harbor and has been since the 17th century.  These days, Old Port shares its space with commercial fishing boats, whale watching charters, cruise ships and oil tankers from around the globe. Commercial Street is your iconic Portland street that parallels the water and is lined with the brick buildings and warehouses that were built following the Great Fire of 1866 to house candle makers and sail stitchers.  One of my favorite aspects of this section of the city is the cobblestone roads.  Leave Commercial Street and you will find the most adorable tiny cobblestone streets, lined with Portland's eclectic array of shops and restaurants.  the best way to explore Old Port is on foot.  Park at the metered spaces on the street or at one of the parking garages. Note:  Public parking is free on Sundays and Private parking and lots are strictly enforced 100 percent of the time. 

Condos and Docks in Portland

Old Port Attractions

Harbor Fish market - 9 Custom House Wharf-  A portland favorite with the freshest of the fresh seafood market.  They ship lobsters and other Maine seagoods all over the country.  

Maine Narrow Gauge Railroad Museum-  58 Fore Street Museum and seasonal train rides offered.  ($3 admission, $10 rides)

Two Fat Cats Bakery- 47 India Street famous for their whoopie pies

Portland's Fish Exchange- 6 Portland Fish Pier. Old Port's active fishing pier 

East Beach- dogs allowed off leash in off season and outside peak hours in the summer 

Walking path along the water 

A walk around the city can be just the solution to balance all the eating you will be doing.  Of course, you can walk around the downtown area, popping your head into various shops and cafes along the way.  If you want something a little more "park-like", head to one of the promenades.  If you bring your dog everywhere like I often do, this is a great place to let your dog off leash or to enjoy some green space in the city. 

Eastern Promenade- best views in the city!

Parks and trails among the promenade 

Eastern Promenade-  Overlooked by tourists, this one has the best views.  On one side, you have Victorian houses now converted to condos and apartments.  On the other side, you have 68 acres of hillside parking, various parks, walking trails, and beaches.   This is a great spot for walking, picnicking, and enjoying the views.  Eastern Beach allows dogs off leash outside the normal hours or in the off season.  There are also sections of the hilly parks here dogs are allowed off leash.  There is a nice paved path following the water where runners and walkers were out enjoying the day. 

Western Promenade- It has benches and nice views.  Often where tourists first come but the Eastern Promenade was much more scienic with some of the best views from the city. 

The best part about Maine- the food!  

I have stopped in Portland on my way to Acadia, headed here for a lobster conference, and have driven here for a weekend away.  Whatever the reason and even if you are just passing through, plan on having at least one meal here.  As someone who spent 48 hours eating their way through the city once said "I had heard about a few great places to nosh in Portland, but for the love of Jenny Craig, the number of good restaurants in a city this size is absolutely criminal". 

 As I enjoyed my coffee and quiche on Sunday morning, discussing the days dining options, I stopped to remark to the barista how just about every restaurants had a 4.5 to 5 star rating. What she told me next, really made a lot of sense.  You see, all of these amazing restaurants packed in this little city,  it is a perfect system "there is so much competition now only the amazing restaurants survive".  You have to make some amazing food to survive the competitive food scenes and high demand of Portland.  Why is Portland growing so quick?  A lot of the big chefs are leaving the bigger cities to see what Portland Maine is all about.  

The main thing I noticed about almost all of the restaurants was there size.  They are all very small with limited dining spaces.  What does this mean?  They aren't trying to crank out meals for 200 people at once,  The 50 people who get a seat are getting the chefs full attention.  Quality takes premise over quantity and lets be honest, it just adds to the trendiness and the scene when you have to scout around at all the packed restaurants for dinner reservations. 

Sampling of where we ate 

Fodor's Recommended (Katie Wanders eaten and approved) 

BaoBao Dumpling House ($):  I wrote a whole post about these delicious dumplings.  Delicious authentic dumplings at a reasonable price

Duckfat ($) Duck fat–fried Belgian fries, cut from Maine potatoes.  Small pub-like burger parlor at the end of the block also known for their milkshakes.  We got the kale salad and the poutine and it was divine. You must stop here for the french fries. 

The Honey Paw ($):  From the owners of Eventide (one of Portland's most talked about restaurants).  This spot is the modern pan-asian joint next door to Eventide.  Handmade noodles, curries, and your favorite New England flavors.  We had an order of the wings (that were big!) and a noodle dish.  The homemade noodles were amazing 

Mash Tun ($):  Mostly a bar with some delicious food on the menu.  Great burgers and sandwiches for a great price.  Impressive beer selection (especially local taps!)

The Holy Donut ($): Again, another "Must Stop When In Portland".  Potato donuts..... The chocolate sea salt was SO delicious. 

Other Fodor's Favorites 

Becky's Diner ($)

El Rayo Taqueria ($)

Elevation Burger ($)

Eventide Oyster Co. ($)

Five Fifty-Five ($$$)

Flatbread ($)

Fore Street ($$$)

Gilato Fiasco  ($)

Gilbert's Chowder House ($$)

Home Catering Company ($)

Hugos ($$$$)

Local 188 ($$)

Lolita ($$$)

Portland Patisserie and Grand Cafe ($)

Tempo Dulu ($$$$)

Union ($$$)

Walters  ($$$)

Beed, Cider, Mead and Kombucha flight at Urban Farm Fermentory

Breweries, Distilleries, Fermentories

Portland is home to over 40 breweries, from small new microbreweries to the larger more well known like Allagash and Shipyard.  There are several beer tours and busses that will take you around.  You can also conquer a "section", picking a few breweries that are all in walking distance like the Industrial park shared by Allagash, Austin Street, Foundation Brewing and a distillery in the same area.  Another option is to start at Urban Farm Fermentory and walk on over to Rising Tide and Maine Craft Distilling.  A lot of different options whether you want to walk around or take the beer bus.

Tasting at Rising Tide Brewing Company 

Breweries/Distilleries/Fermentories Visited:

Allagash Brewing- Amazing space with free tasting and great beers.  Check out my post on Allagash here (Dog friendly patio).

Austin Street- Beer was okay- small space.  Very cool art and loved their logo and designs (dog friendly).  

Foundation Brewing- Very cool large space.  The beer was good and plenty of room to sit down and enjoy (dog friendly- they even had dog treats!)

Maine Craft Distilling-  Again a very cool space and the guy running the bar was great to chat with.  Loved their liquors and brought a bottle of gin home.  Free tastings.  

Urban Farm Fermentory- Amazing stop with a large rotating tap of Kombucha, Mead, Jun, Beer and Ciders.  The kombuchas were the best and we tried three different flights.  Check out my post here. 

Tasting at Allagash

Farm to Flask at Maine Craft Distilling

I usually try to find the cheaper options for hotels when I travel.  I use the room just to sleep and if I am going to spend my money somewhere, it's going to be on the food not the room.  The other issue I tend to have is trying to find a dog-friendly room as we usually have sweet Olive with us.  All Motel 6s are dog friendly and I was able to find a fair prices Motel 6 about 15 minutes outside the downtown area for $70 (including tax and fees).  If you want something nicer with a little more frills, here are some options to check out that are not your standard hotel chains (which you can also find).

The Danforth ($$) B&B/Inn- stylish inn was once one of Portland's grandest federal style dwellings built in 1823.  Known for its gorgeous rooms and city views. 

Inn on Carleton ($) B&B/Inn- 1869 Victorian with an English garden and fountains 

Morril Mansio ($) B&B/Inn- 19th century townhouse close to the arts district

Pomegranate Inn ($$)- B&B/Inn-  funky modern decor, but 15 to 20 minute walk to Old Port

The Portland Regency Hotel and Spa ($$)- Not part of the chain despite the name.  Served as Portland's armory in the late 19th century.  easy walk to sites 

The Press Hotel ($$$) Hotel- Fodor's Choice- housed in a former newspaper building this boutique hotel is part of the Marriott Group.  

West End Inn ($) B&B/Inn 15 to 20 minute walk to downtown 

Beers on tap at Mash Tun (local beers are underlined)

A weekend away in Portland, Maine is the perfect way to escape the winter blues.  Pick a restaurant, settle in and enjoy some amazing food.  Pick from the many distilleries and breweries and enjoy some local Maine beer and cocktails.  Make sure you stop at Urban Farm Fermentory and bring some of their kombucha home.  If you need a break from all that eating, take a walk along the western promenade.  Only 3.5 hours from home, this is the perfect winter getaway.  Thank you Maine for the amazing treats.  

Coffee and Quiche in the city on a Sunday