The Most Epic Weekender Guide to Portland, Maine

During times like these, you may find yourself gazing longingly out your window dreaming of your first trip after COVID-19. You ask yourself, “Do I want to lay on the beach or have more of an urban escape?” and “Would I rather spend my day hiking or set out on a boozy bar crawl?” Plan no more, because we have the perfect destination just for you: Portland, Maine!

Picture yourself on a walk along the New England coastline. Seagulls glide by in the ocean breeze. You arrive at a beautiful structure: a tall tower of white with a single black band and narrow windows at the top. You’ve reached Portland Head Light, a beloved symbol of Portland, Maine’s enchanting city on the sea.

Maine’s largest city boasts a rich history that offers narrow cobblestone streets and renovated brick buildings that house galleries, shops, cafe’s, as well as an assortment of eateries that will leave you entranced in vacationland.

Follow us as we show you how you could make the most of this small, yet lovable New England city on the coast.

Stay Somewhere “So Portland”

First things first. Let’s hook you up with a sick place to stay! We hand-picked three of our favorite options:

  • A colorful, funky hostel beaming with life for our budget travelers
  • A delightfully charming historic Airbnb for our more private travelers
  • A penthouse suite at the former headquarters of the state’s largest newspaper

If you’re a student or just looking for something low-budget, the Black Elephant Hostel in the heart of downtown Portland is the best choice for you! No longer are the days where you’re forced to sleep on a noisy bed or share a dirty, hair-infested bathroom. At Black Elephant Hostel, visitors will be welcomed with a well-decorated space, along with spotless bathrooms and cozy rooms! As a solo traveler, or visiting with friends, you’re sure to meet someone new here to explore everything that Portland has to offer!

Traveling with family? This Airbnb on West End’s Historic Row is fit for up to 6 guests and is located just minutes away from all the shops and eateries you can imagine! The apartment is perfect for anyone looking for historic architecture, brick sidewalks and cobblestone streets. Stay for a night or maybe a week, but we can promise that you will not get tired of this beautiful neighborhood!

Looking to live it up in style? Look no further than the penthouse suite at the Press Hotel. The hotel takes on delightful designs from its history as the former headquarters of the state’s largest newspaper. On the corner of Exchange and Market streets, its location is ideal for exploring.

Day 1: Lose Yourself in “Old Port”

Nestled right along the waterfront, with 19th-century buildings, fishing piers, and a wide array of restaurants, galleries, boutiques, and bars, Old Port takes the cake in combining quaint, small-town attributes with elements from the hustle and bustle of a metropolis. Everything is walkable and bursting with charm. Here are a few places you can’t miss when you are in this part of town:

Museums and Galleries Galore.

Founded in 1882, The Portland Museum of Art is the largest and oldest institution in Maine! The PMA boasts beloved works of Contemporary, American, and European art. The museum features both famous and local artists in their exhibits, such as Homer, Monet, Cassatt, and many more. Not only will visitors enjoy pieces from all over the world but patrons will also get to view multiple perspectives of the city from this multi-level space. If you are under 21, enjoy the museum for free!

If you are looking for an art gallery that’s off the beaten path, you will not be disappointed by the originality of SPACE. SPACE is a multi-purpose venue, where visitors can watch and experience an eclectic array of music shows, art projects and film screenings that encourage curious community members to engage in dialogue. Enjoy the diverse selection of craft beers and ciders at the bar, while supporting the local artists and future events!

Cafes, Restaurants, and Bars, Oh My!

Start your day with some scrumptious and imaginative donuts made with potatoes at The Holy Donut, Portland’s most popular artisanal dessert shop. We recommend getting there before noon for the best selection.

Looking for that delicious lobster roll you’ve been craving? Portland Lobster Company offers delicious seafood, live entertainment, and an amazing view of the bay. Have a live lobster of your own that you’ve caught? No problem! PLC will cook and serve them as part of your meal. To get the most out of this dining experience, we recommend ordering a fresh lobster roll with one of their many local draught beers.

If you want to catch a glimpse of Portland nightlife, Maps is the place to be! Hidden underground, visitors venture down steps into a cozy space with exposed brick and a variety of old maps, plastered on the walls and ceilings. In the afternoon, patrons can come in to enjoy some coffee shop favorites, such as a variety of teas and cakes. If you’re looking for something more on the savory side, order one of the many incredible grilled cheese, alongside one of their fine selections of craft beer. If you stick along until night, Maps turns from a cozy cafe to a hip atmosphere, filled with great vinyl tunes to keep the good times rolling. We recommend ordering the Vermonter, which combines cheddar and provolone with bacon and maple, as well as onion jam, but just make sure to make room for cake!

When one thinks of Maine, they usually conjure images of lobster rolls, but Sichuan Kitchen makes for an equally incredible meal. Its minimalist interior design makes one feel as though they’ve been transported right into a Scandinavian home magazine, but don’t let its minimalist aesthetic fool you, the authentic Chinese cuisine, filled with the aroma and taste of chili peppers, anise, and cinnamon is anything but minimal. Affordable, with a friendly and approachable wine list, vegan options, local beers, and cocktails, this restaurant makes for a perfect lunch or dinner spot that everyone will enjoy! Savor the Zhong dumplings made with fresh pork and served with chili sauce — we promise you won’t forget them.

Calling all cheese-lovers! Feast your eyes and taste-buds on the greatest selection of cheeses, cured meats, bread and other deli goods you are going to find in Portland! Patrons at The Cheese Shop of Portland are welcomed to order freshly made sandwiches with any of the fresh products that you’ve chosen. With a small, yet tasteful selection of wine, customers are always delighted to bring charcuterie back home. If you are new to the world of fromage, have no fear, for the staff members are knowledgeable and always happy to help the curious and indecisive! It doesn’t get much more Portland than this, so support the local people and food!

A visit to Portland may be incomplete without a visit to Flatbread Company. This supremely cozy restaurant, overlooking the bay, bakes all their flatbreads in a primitive wood oven and claims to introduce people “to the magic of earth and fire, and how that combination can produce incredible tasting pizza”. They’re all about community and organic ingredients, collaborating closely with many of New England’s best farms such as Cider Hill or Valley View.

Snazzy, Local Shops.

Looking for that perfect lamp to match your 70’s aesthetic or a fisherman sweater to show off to your friends? Portland Flea-for-All houses antique, vintage and artisan treasures ranging from mid-century furniture to dish-ware. Visitors will spend hours in this store as they gaze at the cool and eclectic items that are found right here! Come see for yourself and buy that lamp and sweater all for an affordable price!

Visiting during the Winter? Warm-up those toes and grab a pair or few at The Sock Shack! If you like cats, dogs, giraffe’s, or zebra’s, this place has it. Made for men, women, and children, The Sock Shack has a pair that’s perfect for every member of the family. Socks are the perfect present to give to your loved ones or for yourself so visit here and you’ll be amazed by what you find!

Day 2: Build Your Own Brewery Crawl 🚶‍♂️

Did you know that Portland has more breweries per capita than any city in the US? Even if you’re only mildly a beer snob, you should plan to enjoy some great brews here. There’s two great ways to do it — make drinking friends on the Maine Brew Bus or take yourself on this amazing self-guided Portland brewery crawl on the East End! Here’s the list of breweries and distilleries along your route, starting from the South, to the North and back West. We’ve included ratings from our friends at Untappd, our favorite social beer app and “The RoadGoat of Beers”.

  • Sebago — 3.63 ⭐️ 112k ratings
  • Shipyard — 3.48 ⭐️ 734k ratings
  • Hardshore Distilling 🍸
  • Oxbow — 3.86 ⭐️ 181k ratings
  • Maine Mead Works — 3.73 ⭐️ 14k ratings
  • Maine Craft Distilling 🍸
  • Root Wild Kambucha — 4.00⭐️ 1k ratings
  • Goodfire — 4.10 ⭐️ 53k ratings
  • Lone Pine — 3.92 ⭐️ 124k ratings
  • Urban Farm Fermentory — 3.56 ⭐️ 23k ratings
  • Extrava — 3.67 ⭐️ 3k ratings
  • Three of Strong Spirits 🍸
  • Rising Tide — 3.70 ⭐️ 136k ratings
  • Austin Street — 3.98 ⭐️ 88k ratings
  • EXTRA CREDIT (jump on metro 2 🚌) — Allagash — 3.89 ⭐️ 1,167 ratings

Hold Your Tummy Down with a Good 🍔 Base

If you’re going to survive this long day of amazing beers, you’ll need a good food base to keep you going. Our two favorites along the route are:

Duckfat. Bordering between the poutine loving, French-speaking province of Quebec, Mainers know how to cook up a delicious version of their poutine at Duckfat. Opened in 2005, Duckfat has become a Portland staple, serving up locally sourced potatoes fried in duck fat, along with homemade duck gravy, and local cheese, Duckfat does not disappoint. Honing in on their familial atmosphere, Duckfat makes sure to foster human connections through their family-style seating. Try the poutine and panini’s for yourself and let us know how these fair against our friends up north!

Portland Pottery Cafe. Check out to discover one of Portland’s best eats. Located in the front of a pottery studio and supply store, the cafe consists of handmade pottery for sale. Visitors are even able to handpick any clay mug to drink coffee out of! Affordable, fresh, comforting, and delicious, we recommend coming for lunch to try their sweet potato sandwich and classic chili! Don’t forget to save room for their incredible selection of desserts!

Select Field Notes

Probably the most well-recognized brewery among beer snobs along the brewery tour is Oxbow Blending & Bottling on Washington Ave (with two other locations across the state). Oxbow is named after the river bends of Newcastle, Maine and it handcrafts its brews to perfection. Nestled in this hip part of town, Oxbow has both an outdoor and an indoor bar so that patrons can get quick and easy service of its numerous brews on tap. If you’re sick and tired of the oversaturated IPA market, Oxbow sells no IPA’s as its main focus is on farmhouse style brews! Refreshing and charming, Oxbow has it all (except IPA’s)!

Lone Pine Brewing Company takes the cake in being all things Maine! From their branding, labeling, laid back atmosphere, and their cabin in the Maine woods aesthetic, this microbrewery serves incredible beer! While here, visitors are encouraged to bring back some brews home and purchase a couple of flights. Stay for a while and play some board games too on their cozy couches! Insider tip: Goodfire Brewery is tucked in the same building and also has amazing beers.

Founded in 2003 by friends, Jake Austin and Will Fisher, Austin Street Brewery has easily made its way to the top of Portland’s vibrant beer scene. With a quirky and fun atmosphere, there is plenty of seating, games to play, and even outdoor seating to bask in the sun. We recommend ordering the Double IPA Offset, as well as the Patina Pale Ale.

If you’re looking for a more household brand, Shipyard may be for you. Founded in 1994, Shipyard Brewing Company is the largest brewer in Maine. We recommend trying their unique, seasonal brews, such as Blood Orange from January to March, or their Summer ale from March to August!

Extra Credit
We can’t mention craft beer and not mention our favorite Maine brewery, Allagash. OK, OK, OK, we realize that it’s a 20 minute drive outside the city and not part of this walking tour but it’s wicked worth it to make it out there! You probably know Allagash for their solid Allagash White and Black beers, but don’t let this fool you into thinking they only know how to make mainstream beers. Allagash puts out some of the very best and more diverse barrel-aged sour beers anywhere. This belgian-inspired brewery also has a terrific indoor-outdoor mixed space and live music, as well as the best rated brewery tour in New England according to USA Today readers. For a quick bite, check out their on-site food truck.

Day 3: Explore Portland’s Perfect Surroundings

Whether it’s through the forest, oceanside, or rolling hills, Maine’s best trails include all three! Wind through the pristine, secluded spaces where you will be tempted to stop and take it all in forever. So, do as the Mainers do and put on your favorite L.L. Bean vest, perhaps a Carhartt beanie and go outside and experience the beauty that surrounds Portland!

Meandering South Along The Coast

Heading south on Shore Road, you’ll come upon Portland Head Light, the oldest lighthouse in Maine. Situated on the jagged edges of Fort Williams Park, this park is the best spot to catch a view of either the sunrise, sunset, or better yet, both! With a long history that stems from just right after the American Revolution as a means to communicate to maritime pilots, Portland Head Light is still in active use today!

Driving a little further south, you’ll find The Lobster Shack at Two Lights. While they may not have the best lobster rolls in Maine, we suggest the stop at least for the coastal views and eclectic interior decorated with old woodworking tools.

Just a little farther along the bend, you’ll reach Kettle Cove State Park. Whether out on the boat or reading near the shoreline, it doesn’t get much more relaxed than spending a day at Kettle Cove! Setting a prime example of well-maintained, small, state-controlled trails that lead to stunning Maine beaches, Kettle Cove State Park gives a sensation that you are on a secluded beach, away from the crowds of tourists that flock to New England. Go for a swim during the summer time, or even in the winter for the annual polar plunge that is held on January 1st!

A Jaunt North up to Freeport

Head north to Freeport, Maine, where you will find the biggest LL Bean store in the world, open 24 hours a day 365 days a year! We suggest going at 4AM for a slightly surreal experience. On your way, be sure too stock up on amazing barrel-aged brews at Allagash, mentioned in our beer crawl day above.

Just a 5-minute drive from the center of Freeport’s busy shopping district stands Wolfe’s Neck Woods State Park. Located on the Casco Bay on the southeastern side of Freeport, Maine, Wolfe’s Neck Woods State Park is a 30-minute drive from downtown Portland. Well maintained and ready to access in all seasons, the trails are fairly easy and short with a beautiful view as a payoff. We recommend to take your time, take in the ocean air as well as the breathtaking views and don’t forget to bring your dog too!

East to The Islands By Boat

While visiting Portland, take the opportunity to explore one of the beautiful islands off the coast. Portland has year-round ferry service that carries passengers to at least six islands! Find more information here.

The End of a Great Adventure

We’re confident that we’ve loaded you with at least three full days of awesome activities, but make sure to find some new gems yourself too! When you get back from your trip, head to RoadGoat’s Portland page to add it to your travel map and share some of your own tips with the rest of our vibrant travel community. Bye!

Love traveling for the best sights out there? Visit roadgoat.com to find the best destinations for your next trip, or to map everywhere you’ve ever traveled! 🗺️📍

Originally published at https://www.roadgoat.com on April 6, 2020.

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