How to spend 24 hours in Portland.

No. 57 Another quick trip and The Sunday Six!

Good morning!

Last week I went on a whirlwind, twenty-four-hour trip to Portland, Maine for an offsite with my company. Pardon me, the company for which I work. I do not own it. The trip was delightful, very brief, and a great reminder for all of us in New England: awesome places to visit are not far from home. We were there for one night, approximately 24 hours, and I got just enough of Portland to make me want to go back ASAP. Quite ideal! And quite fun.

I had not been to Portland in many years and this visit opened my eyes once again to this wonderful small city barely two hours north of Boston. You could even call it worthy of a day trip! Now, our trip was short and dotted with work meetings so I’ll spare you those details and just get to the good stuff. You’re welcome!

24 Hours in Portland, Maine

Stay

The Press Hotel - If you’re looking for a modern, chic spot to stay that’s also filled with history, then this one is for you. The building was the original home of the Portland Press Herald, Maine’s largest newspaper, so every detail is brimming with fun takes on writing and publishing. A delight for this English major, and ahem, writer. ;) My room was great and the hotel staff was helpful, friendly, and at the ready for whatever guests may need. It’s also located mere blocks from the downtown shopping area and waterfront - perfect!

Press Hotel lobby featuring this cozy, sleek bar.

Portland Harbor Hotel - A few minute walk from where I stayed, this hotel was lovely as well and had a more traditional vibe. A small luxury hotel in the center of Portland, this one reminds me of Boston Harbor Hotel (in Boston) with a similar decor and feel. My team had meetings here so I cannot comment on the overall experience, but walking through it I knew I’d like to book a night or two here in the future. :) It is in the Old Port District which is exactly where you want to be to explore all that Portland has to offer.

Eat

UNION - Wow! This restaurant was fantastic. Located within the Press Hotel, we had cocktails in the bar area followed by a seated dinner (served family style) and I am pretty sure every single person left fuller than they had ever anticipated. The food was so good! And omg their attention to detail regarding my gluten free needs was stellar (thanks in part to my friend who was managing the event overall). I had an incredible meal including a massive charcuterie platter (with GF crackers), a great mixed greens salad, local cod, and lobster. Plus, the most delicious sweet corn creme brulee. Heaven! They also offer breakfast and lunch so next time I’m there I’d love to stop in for their other menus. Everything was terrific and I’m so glad it was so easy to eat there with a dietary restriction.

The Holy Donut - I had been hearing about this spot and their fresh-made “gourmet potato donuts” for years so Friday morning before our activities began I got to try two of their famous flavors. They offer regular donuts and gluten free; I ordered two GF and had them put in separate bags (a friend kindly went for me while I was taking care of some work). I loved the dark chocolate sea salt! The vanilla glazed was great, but I do think the chocolate was my favorite. :) Here’s a pro tip: get there early! They sell out and the line gets very long.

Lenora - OK, I cannot lie. I did not eat here during my trip. However, this restaurant was located very close to my hotel and is the Maine outpost of my very favorite Lone Star Taco Bar in Allston. I can only assume I will love it as much as the original. Yes, the menu is slightly different, but I had a pang of home (and tacos and guacamole) as soon as I saw it while walking down the street. I had to share it with you because I really wish I had stopped there for a snack (somehow) before we left the city. The offer breakfast, lunch, dinner, and brunch so if you’re in Portland right now and reading this, head over for your next meal!

Shop

Commercial Street - Portland is overflowing with cute shops and galleries and restaurants, but the “hub” of it all is located on Commercial Street which is on the National Register of Historic Places (and is directly next to the waterfront). I could have spent the entire trip wandering this area and shopping my way through; however, it’s probably for the best (for my wallet at least) that we ran out of time. While you’re visiting, be sure to go into Edgecomb Pottery - made in Maine since 1976 - a personal favorite for beautiful dishes, platters, mugs, and more all handmade in Edgecomb, Maine.

Go

Portland Schooner Co. - While I do not know how to sail, I do know how to enjoy being on a sailboat and that’s exactly what we did for two glorious hours before returning to Boston. Our team spent the morning on one of the wooden windjammers and sailed along Casco Bay with the warm sun on our faces and not a care in the world. Or rather, that’s how I felt! I love boat rides - being on the ocean is so darn peaceful. And while we didn’t see any sea life (maybe a seal or two?), it was an incredibly relaxing, joyful way to close out our 24 hours in Portland. I highly recommend getting tickets to one of the many sailing trips still available through October.

Clearly, a lot of fun can be had in Portland even it’s a brief overnight stay! I would have loved to stay through the weekend to visit more of the restaurants, shops, and perhaps even squeeze in another boat ride. Until next time! I found out that the Press Hotel is dog friendly. ;)