My Weekend in Portland, ME with Canopy

The inevitable happened… I finally played tourist in Portland! This popular New England destination has been on my doorstep growing up, however I’ve never treated myself to a stay in the city. When the Canopy Portland Waterfront reached out for me to check out their offering over a long weekend, I couldn’t say no! This hotel just opened June 2021, and gave rooms to a much needed area of Portland, the Old Port. If you’ve tried any regional travel in New England, you’ll know that hotel rooms in Portland can be tough (and expensive) to come by. Canopy offers a refined, yet cool, solution for travelers. Follow along below to see how I spent my days in this iconic Autumn destination.

Canopy Portland Waterfront Lobby

3:07PM on Friday

I checked into the Canopy right on Centre Street in Old Port and dropped my bags in the room before quickly heading out to grab a bite to eat just a 4 minute walk down the street at Portland Lobster Company. While there is often a line on busy weekends, they are a pretty well-oiled machine turning out lobster bakes and rolls with a view overlooking Old Port. You can often find them as hosts to live music on the weekends, and all walks of life who are appreciative of one of Maine’s signature dishes.

Canopy Portland Waterfront Guest Room
Portland Lobster Company

4:32 PM on Friday

Immediately after downing a lobster roll, I walked back to the Canopy to see a performance installation on the side of the building! Put on by Portland Ovations in collaboration with the hotel, BANDALOOP shared their innovative vertical performance combining intricate choreography and climbing technology. After the performance, I scooted over to Hunt & Alpine for an afternoon drink before the sun went down. Their space is great for grabbing a cocktail and snacks during the day on weekends with friends.

BANDALOOP performance at Canopy Portland Waterfront
Hunt and Alpine

9:16PM on Friday

Early to bed for me back at the hotel! I rented a movie and snacked on the cupcakes left in my room by the Canopy team before getting some shut-eye.

Rose Foods

8:32AM on Saturday

The next morning I started with a long walk to Rose Foods (roughly 30mins) to get one of their famous bagels and a cup of caffeine. I went with a Classic Nova, but highly recommend the Luxe Lox as well. After turning a few pages in my latest read, I made the walk back to the hotel. I hopped in my car and made my way over to Portland Head Light, about a 15 minute drive from the hotel. This also makes for a great bike ride if you prefer to get around on two wheels.

Portland Head Light

10:17AM on Saturday

Upon arriving at Fort Williams Park, I tucked my car in the lower parking lot by the beach (way easier to maneuver on busier days), and walked the cliffside trail up to the lighthouse. There’s a lookout where I hop over the fence to snap this shot. There is a little path, so you know it is well-traveled. Just be safe! To reward myself for braving the crowds, I made my way back to Old Port and snagged some oysters at Eventide. Don’t forget to also grab their famous hot-buttered lobster roll, and my favorite, the lobster stew.


1:57PM on Saturday

Moseyed back to the room for a power nap and some photo editing. A quick outfit change, and I was ready to hit up the rooftop bar at the Canopy, Luna Bar.

Luna Bar roof deck at Canopy Portland Waterfront

4:01PM on Saturday

I quickly hop in line down in the lobby awaiting the green light from the hostess to head up to the bar. Luna is notoriously busy, so get there early to snag a coveted seat on the outdoor roof deck (heated, of course). Cocktails and small bites are a must when taking in the views. The bar program is thoughtful, and even includes mocktails for non-drinkers. And we were thoroughly impressed by the mushroom bao and gnudi with seasonal touches.

Cocktail hours spread at Luna Bar
Oysters and drinks at Blythe & Burrows

8:17PM on Saturday

After priming our stomachs at Luna, we made our way to Blythe & Burrows on Exchange Street for oysters and, yes, more drinks. This dimly lit bar makes for a date spot, or a meeting place with friends. They have several tables that can accommodate larger parties through the secret passageway (through the book case), and if you make it up to Portland during the week, they have $1 oysters on Wednesdays. To no one’s surprise, we shut the bar down, and I made the 7 minute walk back to the hotel.

10:54AM on Sunday

The next morning called for a little editing in bed and then a workout in the hotel gym. After showering and packing my things, I made my way downstairs to Salt Yard for brunch before heading home.

Breakfast from Salt Yard at Canopy Portland Waterfront

If my schedule above is any evidence, Portland makes a great weekend getaway. There are plenty of amazing things I didn’t have a chance to do this time around, but are worth a trip back. Most notably: dinner at Scales, catching a concert at Thompson’s Point, uni spoons at Izakaya Minato, a sunset sailboat charter, and cocktails by candlelight at Bramhall. Looks like another stay at Canopy is in my future ;).

Special thank you to Canopy Portland Waterfront for sponsoring this amazing weekend!

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