HELLO, PORTLAND, MAINE!

An easy hour and 45 minute drive (or 2.5 hour train ride) from Boston, Portland is the perfect New England day trip for those craving a unique taste of Maine. While Portland still embodies the deep Northeast experience of fishermen and L.L. Bean boots, over the past few years artists, brewmasters and chefs alike have been flocking to this city to shake up the old with the new. 

Whether you visit Portland in the summer or winter months, you’ll be sure to have a great time. In the summer, the city is filled with lively crowds, colorful street art, and lots of action on the water. However, when the snow starts falling and fires start glowing, Portland transforms into one of the coziest cities in the country — just don’t forget a hat and scarf! The great part about Portland is that it’s super walkable. Once you park your car, you can roam around the entire town, taking in the colonial architecture, coastal views, small town charm, and big city foodie scene. 

Speaking of foodie scene, my favorite part of Portland is that it’s a food lover’s dream! There are mouthwatering food options all over town. Whether you’re in the mood for a classy dining affair or gourmet food trucks, Portland can definitely satisfy your cravings. 

The historic seaside roots and trendy (almost hipster) vibes work in unexpected harmony to create a city like no other. Portland is a place that everyone must experience at least once in their lifetime. So whenever you decide to check this unique town off your bucket list, here is my itinerary for the perfect day in Portland, Maine.

Portland ME 04101 DiMillos Marina
DAY TRIP ITINERARY:
  1. Brunch at The Front Room ⇢ Try the Blood Orange Mimosa / Blueberry Silver Dollar Pancakes / Eggs Benedict
  2. Walk off food by strolling around Fort Allen Park then down Fore St to the Old Port district.  •  Fort Allen Park is a lovely spot to relax and take in the scenic water views.
  3. Explore the shops on Exchange St.  •  Whenever I visit Portland, I always stop by Sherman’s Maine Coast Book Shop. Founded in 1886, this is Maine’s oldest book store! I love skimming through the discount travel guides and cookbooks at the front of the shop. Made in Maine is also an adorable shop that offers unique gifts and home goods created by local Maine artists.
  4. Say hi to Our Lady of Victories in Monument Square then stroll through Downtown to the Portland Museum of Art. 
  5. Grab dinner at one of the many delicious spots in Portland! I couldn’t pick just one so here are my favorites:
  • Boone’s Fish & Oyster House  •  Relaxed seafood spot with two outdoor decks and views of the sunset on the Portland Harbor. The seafood is so fresh that your server can show you which boat brought in your meal. ⇢ Order the Oysters on the Half / Classic Lobster Roll
  • Taco Escobarr  •   Fun, funky and colorful Mexican restaurant ⇢ Toasted Coconut Margarita / Chipotle Sweet Potato Taquitos / Al Pastor & Fried Avocado Soft Tacos
  • Eventide Oyster Co.  •  An absolute must visit if you’re a fan of oysters and lobster rolls! Sit at the counter along the windows to people watch while enjoying some of the best seafood in New England — definitely put your name on the list early as most people wait 2-3 hours for a table. ⇢ Empire of the Sun Cocktail / Oysters / Brown Butter Lobster Roll (this thing literally melts in your mouth!)
  • Central Provisions  •   Super popular upscale tavern offering tapas-style plates  — highly recommend making reservations in advance! ⇢ The Swizzle / Spanish Chopped Salad / Fried Maine Grains Polenta / Confit Tuna Crostini

6. Wrap up the night with dessert and martinis at the Bar of Chocolate on Wharf St, or enjoy creative cocktails and cheese boards at The North Point. to the

Portland ME 04101 Exchange Street Shops
Portland ME 04101 Shermans Maine Coast Book Shop
Portland ME 04101 Monument Square
OTHER GREAT THINGS TO SEE & DO:
  • J’s Oyster  •  Relaxed restaurant/bar located on the waterfront. This place offers a wide variety of local seafood including MASSIVE lobster rolls and salty oysters. This place is so good that Anthony Bourdain said J’s is the kind of place he wished he had in his own neighborhood.
  • The Holy Donut  •  A Portland staple that was named one of the top ten best doughnut shops in the country. This place offers 16 varieties of handmade potato doughnuts daily.
  • Check out the brewery scene!  •  Portland is home to a number of highly-rated breweries including Rising Tide, Oxbow, Bissell Brothers, and Portland’s original Allagash.
  • Island hop around Casco Bay which is home to 220 islands.  •  Take a short ferry ride to Peak’s Island, a local favorite where you can bike around and explore the colorful cottages and pebbled beaches. ⇢ See ferry rides here.
Portland ME 04101 City Hall
Portland ME 04101 Js Oyster