A Weekend in Portland, Maine
This historic seaside town is a short drive from NYC.
Portland a place for all types of lovers: food lovers, history buffs, animal and nature lovers. Foodies, artisans and nature-lovers flock here. Massive cruise ships dock here daily so their passengers can take in the historical significance. It is a place many travel thousands of miles to visit and its busy port welcomes massive cruise ships daily. An hour and a half flight or a five-hour drive from NYC, laid-back Portland feels worlds away from the fast-paced and bright light of NYC.
With its turn of the century architecture and booming foodie scene and a dress code that is part craft beer hipster, part beach town, the casually cool local Mainers welcome you. The downtown is dotted with art museums, cobble stone streets, brick buildings housing a casual and cozy shopping district and an up and coming food scene consisting of much more than the famous lobster.I spent a long weekend exploring the many and diverse activities this seaside town has to offer.
See here is how I made the most of my long weekend in Portland.
DAY 1
Start DAY 1 with a tour of the Victoria Mansion. A magical home built by two New Orleans hoteliers in 1860. With its sculpted wood accents, etched stained glass and Gothic Revival architecture, furnishings and artwork, this is a must see.
Next, head to the Portland Observatory, the last remaining maritime signal tower in the U.S. It sits on the highest hill in the city. So, after you trek the seven stories learning about it’s history you are rewarded with 360 degree views.
Stop and grab a bite to eat at Otto Pizza a creative pizza joint with a signature line of soda. The pizza choices range from vegetarian butternut squash, ricotta and cranberry to a meaty pulled pork and mango to spicy hot pineapple salsa, bacon and jalapeno. Pizza that's unlike any other in the best way possible. At Otto’s the pizza is creative and unique. I enjoyed the mashed potato, bacon and scallions, and the blue cheese, roasted pear and arugula.
Next, take a walk through the neighborhood of large Victorians turned multi million dollar condos until you reach The Eastern Promenade, a large park with sweeping views of Casco Bay, just down the hill, from the Portland Observer.
Make your way back downtown stopping by Two Fat Cats for a slice of blueberry pie. Make sure you get there before 1:00pm before they are all gone. If you miss it, head to The Old Port Candy Co. for fudge or chocolate covered blueberries and more.
If you want to take in the most sights in the least amount of time take a city tour with The Portland Explorer tour or The Real Portland Tour around town and out to Cape Elizabeth for the quintessential opulent coastal Maine neighborhood of rocky shores, lighthouses and lobster rolls.
When you return, have dinner at one of the many downtown restaurants or craft breweries such as Fore Street, a farm and sea-to table, or Little Tap House for craft beers and lobster mac and cheese or delicious steak.
DAY 2
On DAY 2, begin early with breakfast at The Holy Donut. Famous for creating a donut made of potatoes, yep, potatoes. They are delicious and if you don’t get there early be prepared to wait in line, a very. long. line. They have a wide variety of flavors like blueberry, maple bacon, lemon and coconut.
Before the shops open check out the fish market at The Portland Fish Exchange, as the boats come in and the restaurants go shopping for fresh fish to add to that days menu.
Once the shops open, the Old Port/Waterfront district comes alive. Check out all the different shops filled with home decor, souvenirs, clothes and more. There are also artists selling original crafts street side. These vendors are required to make their own crafts so these are not goods you can get anywhere.
Take your lunch break at the Portland Lobster with a lobster roll and a beer or any number of seafood dishes and beverages. An amazing house band plays throughout the day.
Spend the afternoon on a cruise around the coastal islands with Portland Discovery Land & Sea Tours or perhaps hop on a lobster fishing boat and head out to catch your own which you can then take to the Portland Lobster Company restaurant on the pier where they will cook it up for you.
At the end of the day, if you’ve had your fair share of seafood head to Terluglia, in a residential neighborhood along Washington Street. Terluglia serves delicious dishes of a Southwestern BBQ fusion with Caribbean flavors. Every Sunday is neighborhood night serving a smaller menu but the items vary from the standard menu.
If you have extra time, check out 4-half day trips within 30 miles of Portand, ME.