Visiting Portland Maine in May

From a Texan’s point of view, when visiting Portland, Maine, in May, you will want to bring along an umbrella, a sweater, an empty stomach, and good walking shoes. Read on, my friends!

My husband and I flew to Boston, received a Mitsubishi Outlander Sport to drive for our road trip to Portland. The minute we got on the highway, I felt we were going back in time. Going back into Fall, that is. The trees still had their beautiful fall colors. In Texas, spring has already sprung. Not a bad thing at all, just a little surprising to me because I hadn’t been to Maine in May before. We knew we would have some cold weather and enjoyed the drive and the scenery.

So, I went to Portland for the WITS19 Conference, and my husband went along to do some sightseeing and to eat good food! We were there for six incredible days.

If you visit Portland, Maine, in May, you’ll want to pack a few things.

You know the month of May is unpredictable – it’s the month that’s so hard to plan for, no matter where you go. In some parts of the U.S., the month of the year seems to be when winter is over, and spring hasn’t started to show. I have visited some states where all winter sports are closed, and spring/summer sports & adventures haven’t begun yet. However, when visiting Portland, Maine, in May, you can rest assured everything is operating. The weather might not be ideal, but there is undoubtedly a lot going on.

From what we saw, all the restaurants were operating and packed with locals & travelers. The hotels were thriving with guests, bus tours were abundant, and people were walking around town everywhere.

The hotel we stayed at (AC Hotel of Marriott) had a happy hour each day, and guests and locals seemed to be indulging. It’s one of Portland’s newest hotels with large windows facing the seaside where everyone looking in could see what was going on. It’s a gorgeous hotel, and I’m sorry I didn’t get a photo.

Driving around Portland, Maine

I hope you know how to parallel park if you drive to Portland. We didn’t particularly like that because neither of us is good at parallel parking. We walked everywhere or had the hotel shuttle drive us to nearby places. There’s not a lot of free parking either. We also took advantage of the hotel’s valet parking for $28 a day, where we could come and go as we pleased. In some areas, you can park free AFTER 6 pm; however, you must move your vehicle before 8 am the next day, or you will get ticketed. FYI.

Restaurants in Portland, Maine

I mentioned above that Portland is known for its good food and excellent restaurants. Tracy and I visited many, including Duckfat, Hot Suppa for breakfast, Old Port Sea Grill, J’s Oyster Bar, but Scales stood out for both of us. The halibut and haddock were excellent, the service was awesome, and the view was spectacular. Scales is an upscale restaurant that our hotel recommended. So now, I recommend you go there when visiting Portland, whether it’s in May or not.

Things to do in Portland, Maine

Besides what I’ve already mentioned above, one of the things we did was visit one of Portland’s parks. This park was right beside the beach. Remember, we are from North Texas, where no beaches exist. My favorite thing to watch was dogs and their owners having fun on the beach, throwing sticks out in the water for the dogs to fetch. Everywhere you walked, there were owners with their dogs – big and small, but mostly big dogs.

If you visit there, tune into PortlandOldPort for all the latest news and activities in the city. They are up-to-date with all the fun stuff!

Wine & Beer Tours in Portland, ME

All kinds of tours are offered here, such as food tours, wine tours, brewery tours, house tours, and more. While attending the WITS19 Conference, I was lucky to score a free bus tour on the Maine Brew Bus, where we visited a brewery, winery, and distillery. The Rising Tide Brewery has some homemade killer beers. Cellardoor Winery had the most precious room with pink couches, chairs, flowers, and beautiful chandeliers (my favorite), where we sampled some of their best wines. Stroudwater Distillery had some great spirits to taste and gave us a sample of their freshly made coffee liqueur.

Depending on what you’re going there for, visiting Portland, Maine, in May may not be the ideal time, but rest assured, the town is open for business. I would travel to it again with my family or solo.