On a rainy day in Portland, Maine, the normally lively city takes on a serene and peaceful charm. The pitter-patter of raindrops against the cobblestone streets and historic buildings creates a soothing atmosphere. At the same time, the city’s eclectic cafes and shops provide a cosy escape from the drizzle. Choosing to embrace the elements, a rainy day in Portland offers the opportunity to discover the port city’s hidden gems uniquely and memorably. Pack your rain jacket and boots. With so much to see and do, you won’t even notice the rain on this itinerary for one day in Portland, Maine.
Table of Contents
Morning: Harbor and Wharves
Breakfast at Salt Yard Cafe & Bar
It’s hard to recommend lunch anywhere other than the Salt Yard Cafe & Bar. The atmosphere and attention to detail make this exquisitely decorated establishment a worthy stop in any traveler’s itinerary. Fantastic food, reasonable prices, lots of flavor, and great options for breakfast and lunch. It is hands down the best morning meal I’ve ever had in a hotel restaurant. Their salted caramel latte is emotional comfort in a cup, a soul-soother on a rainy day.
Although it is located inside the hotel, the restaurant is on the street level and easily accessible from the sidewalk.
Exploring Portland’s Old Port
No visitor wants to miss the historic, picturesque harbor area. Portland’s Old Port is the shopping and restaurant district with lots of little boutiques and restaurants strewn around old cobblestone streets. A food lover’s mecca, the seafood delights of coastal Maine can be found around every corner.
While exploring the waterfront might be less appealing when it rains, plenty of shops are around to browse. It is easy to lose yourself in kitchen supply outlets, ceramics stores, and the quaintest gift shops such as nautical-themed Shipwreck & Cargo.
Afternoon: Lighthouses, Museum and Cruises
Lunch at Gilbert’s Chowder House
Don’t be deterred by the retro décor of this restaurant. This restaurant tops every list for a reason. Gilbert’s Chowder House is renowned for having one of the best chowders in town, and let me tell you, that reputation is well deserved. It even got the approbation of my chowder-connoisseur partner.
Here’s a tip. Get the super seafood chowder (It has double shellfish!), but skip the bread bowl. These soups are really loaded. I took a medium bowl and got at least two lobster claws!
Pay a visit to Maine’s oldest lighthouse: Portland Head Light
A little to the South of Portland is one of the region’s main attractions. Although it is easier to take advantage of the surrounding hiking trails when the weather is sunny, there’s an implacable sense of realism to visiting the lighthouse on a drizzly day.
Waves crashing against the jagged rocks of the cliffs, no picture does justice to actually being there. If you really want a great perspective of the beautifully restored building, make sure to walk the cliffside loop. If you have the chance to visit Cape Elizabeth when the museum is open, it is pretty interesting and worth the 2 $ admission.
Getting inspired at Portland Museum of Art
Being the perfect image of what a regional museum should be, Portland Museum focuses on art about Maine and art created by Maine artists. It gives visitors a unique chance to see all of the beautiful interpretations of the state’s outdoors from many perspectives over decades. Moreover, there is a contemporary art floor and a permanent collection of world-class master paintings. They are a few works from Warhol, Homer, and Claude Monet, among other artists.
This gem of a Museum lets you spend a lovely couple of hours inside and enjoy how beautiful Maine can be from another perspective.
Going on a sunset cruise around the nearby islands
A sunset tour in the rain? Why not? A few companies offer sunset cruises in the summer, but if I had to pick one, I’d choose Portland Discovery Land & Sea Tours. Their sunset tour takes you to the inner islands bordering Portland. This is a nice way to sightsee the more inaccessible lighthouses, the evening breeze in your hair, and Portland shimmering in the distance.
It can get foggy on a rainy evening, but the phenomenal crew makes up for it and create an unforgettable experience.
Evening: Restaurants and bar hopping
Having dinner at The Green Elephant
Many people talk about going to Becky’s Diner when looking for a place to eat in Portland. While it is a good choice, other options are available. I found when walking around Portland’s Old Port that there were a lot of Asian restaurants for such a small city. While it might be popular among locals, The Green Elephant is genuinely a hidden gem for Portland first-timers.
Besides having good decor and seating, this restaurant is a vegetarian paradise in the heart of the city. In fact, everything on the menu is vegetarian! But don’t let that intimidate you; this pan-Asian bistro knows exactly how to create meat-free meals with the perfect amount of spiciness.
Create your own bar crawl and live the classic bar hopping experience in Portland
Portland has an embarrassment of riches when it comes to bars, making it inarguably one of New England’s most vibrant and diverse scenes.
While drinking your way through the red-brick streets is the best possible way to end your day here, you can’t possibly go into every pub you see. Eventide Oyster Co, Lincoln’s, Maps and Nosh are all classics and a walkable distance from each other in the Old Port. If you’re willing to go a little farther, Bissell Brothers Brewery is a little more to the west and a real show-stopper.
Best time to visit Portland
I visited the port city during the spring, and let’s say it was a bit rainy while I was there. The best time to visit Portland (and Maine) is from June to August. While eating lobster rolls is a pleasure at any time of the year, it feels better with a light summer breeze on your skin! (The briny wind of April forgotten.)
How to get around Portland, Maine
The easiest way to travel around Portland is to have a car. Although parking can be tricky around the old port, there are affordable parking lots just a few blocks away. Also, if you’re staying at a hotel in the historic district, check with them first as they usually have a special rate for their guests. If you don’t have your own wheels, there are other options. Bike rentals, buses and ferries typically get you where you want, even the Portland Head Light!
Where to stay in Portland?
The obvious choice for me is the Canopy by Hilton. The hotel has a beautiful terrasse overlooking the harbour and the delightful Salt Yard Cafe & Bar I mentioned above.
How to get to Portland?
While Portland has an airport, it is easily accessible from anywhere in New England. Coming from nearby Montreal, however, I must admit that the roads connecting the two cities were not the most straightforward. There was a lot of driving through cottage country and country roads.