48 Hours In, Travel
Leave a Comment

48 Hours In | Portland, Maine

Often confused for the OTHER Portland in the USA, Portland, Maine has been quickly making a name for itself in the food culture and music scene. In the past few years restaurants have been popping up left and right along with well known chefs making this small New England city their new creative outlet (as well as focusing on keeping it local!) Portland has also seen an increase in big name music groups venturing up north as the city becomes a big name in the country.

So grab your Bean Boots and book by native Mainer Stephen King and venture to up to the small but eclectic city in the countries most Northeast state.

Wakeup: Start your day with an exquisite coffee or tea from Arabica on Free Street in the center of town. A local and organic coffee shop that offers various pastries and various brews of coffees and teas, this is a great spot to start your morning. With brick walls and gorgeous wooden tables, you can make yourself feel at home for a couple hours or 5 minutes. If there’s a line out the door, don’t run away – it’s worth the short wait!

Waterfront Walk: The Old Port, known for its cobblestone streets, small boutiques in beautifully refinished brick buildings, and the docks where fishing boats still come back home after a day of fishing, is where it’s okay to wander mapless to pass a few hours in the morning. You’ll find a mix of touristy shops filled with blueberry and moose laden trinkets to locally made totes at Sea Bags and jams and dips at Stonewall Kitchen (you can also check out one of their cooking classes if it sparks your interest!!) In the evenings, the Old Part is filled with young and older party goers alike. Although the majority of the bars are filled with college aged kids, you’ll find a few hotspots with live music and great draft beer filled with a more mature crowd. While the further you go towards the outskirts of the Old Port into Downtown you’ll find a more and more options for local, low-key places to spend an evening (but we’ll get into this later!)

photo by: portlandmaine.com

Across the harbor: You have many options to view the beautiful city of Portland from the waterfront from kayaking, sailboat, or various ferries that will take you to the Casco Bay Islands. A personal favorite is Peaks Island. In the summer, they celebrate Reggae Fest every Sunday afternoon. You can avoid the craziness by going any other day or if Sunday is your only option, just walk off the boat and up the road where you’ll find Brad’s Bike Rental where you can rent a bike and helmet for just $10. If he’s not there, you can leave your ten in a jar outside (as faith in the honesty of humanity still exists on this little island). Pedal around for the morning stopping into various hidden coves, small fields, museums, and small lemonade stands. Stop for a cup or two and keep this American tradition alive! Also, don’t miss out on taking your own honey home at Evergreen Ledge from Peaks Island Honey Company. All you have to do is leave $3 in the coffee can . . .

photo by: peaksislandgolfcarts.zohosites.com/

Late Lunch: Located right on the waterfront, Flatbread Company offers a full menu of stone-oven baked pizza using local and organic ingredients. They’ve been around for awhile and have been ahead of the game using organic and local before it was just the ‘’normal thing’’ to do! Originally located in Amesbury, Massachusetts they’ve grown to establish nine other locations around the states – as far out as Paia, Hawaii, too!

photo by: flatbreadcompany.com

Longfellow Books: A local haunt for literature aficionados, this tiny independent bookstore is a popular book launching spot for local writers. Featuring a large selection for such a tiny place, Longfellow Books is located on 1 Monument Way just off of Monument Square in Downtown. Take a peek and see if anything catches your eye! Maybe you can take home a less traditional momentum from your holiday and support a local business while at it!

Downtown Arts District: Wander back up through the Old Port towards the Downtown Arts District located mainly around Congress, Free, and High Street – however, it also branches out towards Cumberland Ave (near the bay) to the waterfront. Pop in and out of various boutiques, art galleries and if you’re lucky enough to be there the first Friday of the month you’ll be able to see local artists and vendors setting up shop to sell their goods through the late afternoon / evening. 

Portland Museum of Art: Despite not being the biggest art museum on the East Coast, the Portland Museum of Art buildings offers a unique history of their own. The PMA is located in three historical buildings:

  • Charles Shipman Payson Building, built in 1983 by architect Henry N. Cobb of Pei Cobb Freed & Partners, post-modern design
  • L. D. M. Sweat Memorial Galleries, built in 1911 by John Calvin Stevens, Beaux-Arts design, restoration completed in 2002
  • McLellan House, built in 1801 by John Kimball Sr., Federal period design, restoration completed in 2002

Offering a twist of architecture to the art museum, the PMA keeps a constant gallery containing local Maine artists such as Winslow Homer and Marsden Hartley as well as more well known European artists such as Monet, Picasso, and Renoir.

The PMA also has a changing exhibition that brings fresh faces into the limelight. Educational programs such as art classes, musical performances, and lectures are also offered by the PMA.

photo by: portlandartmuseum.org

American Traditions: There’s something about spending an evening at a traditional American baseball game that makes it truly feel like summer. The Portland Sea Dogs, the AA affiliate of the Boston Red Sox, call Hadlock Field their home just outside the downtown area of Portland. Ticket prices are low (at $10 or less) and games are long. So sit back, grab a famous Sea Dogs Biscuit and maybe a slice of pizza or a more traditional ballpark frank (hotdog!) and enjoy one of America’s favorite pastimes . . . and maybe you’ll even catch a fly ball!

photo by: milb.com

Caiola’s: If you’re not up for the pizza or hot dogs at the ballpark, then sneak out of the game just early enough to snag a bite before the kitchen closes at Caiola’s at 10pm on Friday & Saturday. A local neighborhood hotspot in the West End (near Hadlock Field!), you’ll find a welcoming atmosphere with a full menu to satisfy those hunger pangs. Offering fresh Maine seafood and fish to generous cuts of steak and chicken, the menu is constantly being reinvented to keep things fresh and creative. Described as ‘’upscale comfort food’’ by the Washington Post, this is the place that’ll put the cherry on top of your first day in Portland, Maine.


Breakfast: Bintliff’s American Cafe is located in Bay Side of Portland’s downtown area. A lesser known breakfast spot by tourists, it’s definitely a better dining experience than its breakfast counterpart on the waterfront that gets most of the attention: Becky’s Diner. Bintliff’s offers a range of basic breakfast menu options to more extravagant combinations to jumpstart your palate in the morning. Try their homemade corned beef hash or classic two eggs breakfast if you’re feeling a bit more traditional – or venture further down their menu for their benedicts, waffles, or french toasts. Maine blueberry buttermilk pancakes also make the menu, don’t worry.

Deering Oaks Park: Portland Farmers Market has various locations throughout the city depending on the day. You can find them located in Deering Oaks Park late April through November on Saturday mornings – even as early as 7am! Local chefs also find time for the market in order to keep up with the changing seasons and look for fresh produce to use in their menus. You’ll be able to find a mix of fruits and vegetables, herbs, plants and flowers, honey and maple syrup, jams, cheeses and milks, hanging baskets, meats, and so much more!

Deering Oaks Park is also a relaxing place to walk around, feed the ducks, or take a blanket to read in the park away from downtown while not having to go far. Also home to a baseball diamond, tennis park and pond – its a fun place to be active or simply enjoy the morning. The park was designed by architect Frederick Law Olmsted who designed various parks throughout the country. However, his most famous one: Central Park in New York City, was inspiration for the small park in the center of Portland, Maine which he designed 22 years later.

photo by: corey templeton @ portlanddailyphoto.com

Coffee or Tea?: It’s always a hard decision. On your way towards the Eastern Prom, stop into Coffee By Design on India Street (they have various locations throughout the city!) or Homegrown Herb and Tea on Congress St. They offer local and organic products and a great cup o’ joe or tea! Take it to go and continue your journey up to some of the best views in the city.

Munjoy Hill / Eastern Prom: After a morning in the park, venture over to Munjoy Hill for some bay views from one of the highest point in the city. A grassy knoll lined with houses and small boutiques popping up left and right, this is a fantastic place to enjoy the afternoon watching the boats (big ships to the tiny sunfish sailboats) passing through the islands or coming in and out of the harbor.

On your way up stop at The Portland Company Marine Complex which is home to the Maine Narrow Gauge Railroad Co. & Museum as well as different markets that use the space in the building.

More shops call Munjoy Hill home such as: Ferdinand and Home; Angela Adams; Cyclemania; Maine Mead Works; Casco Bay Glassworks; The Front Room; and the Blue Spoon for some local hot spots. photo by: skyscrappercity.com

Duck Fat: Once you’re craving some nourishment, head down the hill onto (43) Middle Street where you’ll find Duck Fat. A brick walled, bar-stool laden restaurant featuring paninis, soups, and salads. The perfect place for a quick bite to eat with plenty of places to grab a seat.

Don’t miss out on owners Nancy Pugh and Rob Evans reason for opening their restaurant in the first place: hand-cut Maine potatoes fried Belgian-style in duck fat, tossed with their seasoning salt and served in a cone with your choice of eight homemade dipping sauces – doesn’t it just make you drool?

So swing by and grab a side of fries and a meal at one of the best places in town that makes delicious homemade food from some of the best quality ingredients. This includes nearby vendors such as Standard Baking Co. for their panini bread and Coffee By Design for their cup of joe.

photo by: justaddcheese.com

Portland Head Light: A trip to Portland, Maine without venturing into Cape Elizabeth to visit the Portland Head Light in Fort Williams Park, isn’t a trip to Portland. Although you’ll be venturing from the city parameters, it’s well worth the short drive for the unlimited ocean views. At no cost to enter the park (just take out what you take in!) walk around the grounds and visit the various forts hidden throughout. The Portland Head Light stands along the cliff creating a beautiful backdrop for your portraits from Maine (and if its around sunset, even better)! Their award winning museum contains a number of lighthouse lenses and interpretative displays.

Fort Williams Park is also usually filled with sporting events such as soccer matches, baseball games or children playing in the park near the beaches. Wander around, take your time, and enjoy.  photo by: peterurbanski.com

Dine Out: Upon returning to the city, stop at Hot Suppa for some southern spice up in the land of yankees. Offering a $1 Oyster special Tues-Saturdays from 4-6pm, start your dinner off with a plateful as appetizers. But don’t fill up too much because their menu is mouthwatering and full of not-to-miss options. Inspired by New Orleans, they take the traditional New England seafood and give it that southern twist such as the NOLA Shrimp Cocktail, NOLA style BBQ shrimp, and ½ shelled oysters. Also on the menu: catfish, fried green tomatoes, poor boys, and fried chicken and a waffle.

If you’re looking for a little less spice, then head up the street to Local 188. Inspired by Spanish cuisine, they offer various tapas, raciones, and cenas (individual appetizers, shared appetizers, and dinners) and as their name gives away, all the food they serve is local. From seafood chowder to a hanger steak or spanish tortilla to local mussels you’ll definitely be able to find something that calls your name.

Drinks: (Grace) To keep the evening going, head back up Congress Street and visit Grace. You’ll hear yourself hold your breath as you walk through the doors into this Gothic Revival style church that has been reborn as a restaurant in the heart of Portland.

Still adorned with stained glass windows that now sit above the open kitchen, pews line the edge of the restaurant creating seating for the tables on the first floor while a more modern touch has been brought to the second floor for dining experience.

‘’The building dates to before the Civil War, which is important because so many buildings of that era were destroyed in the big Portland fire of 1866,’’ states the restaurants website about the history of their building.

While being blown away by the architectural details from the mid 1800’s that still remain, order a drink off their wine, beer, or cocktail menus at the bar – ironically located where all the churchgoers would come to repent their sins, all these years later a bar sits confidently in the middle waiting for their patrons to order up a few drinks and maybe confess to one of their sins or two.

photo by: restaurantgrace.com

(Sonnys) If you still want to keep the night young, pop on over to Sonny’s located at 83 Exchange Street. A sister bar of Local 188, Sonny’s bar and lounge offers local with a latin twist. They offer an exquisite cocktail menu with that latin vibe – they even have Pisco Sours!

photo by: corey templeton @ urbanspoon.com

Live Music: Great places for live music vary from neighborhood to neighborhood. It all depends on your personal music taste, so as for recommendations – I won’t venture into that, but I will give you a link of awesome places to check out on your own, see who’s playing and follow your musical vibes: http://www.portlandmaine.com/maps/live-music-venue-trail/

photo by: statetheatreportland.com


Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out / Change )

Twitter picture

You are commenting using your Twitter account. Log Out / Change )

Facebook photo

You are commenting using your Facebook account. Log Out / Change )

Google+ photo

You are commenting using your Google+ account. Log Out / Change )

Connecting to %s