How to Spend a Birthday in Portland

Portland can be pretty busy in the summer with tourists, so we didn’t visit as many shops. But it’s also one of the nicest times to visit. The pleasant weather allows for enjoyable outdoor activities like hiking in the nearby mountains, exploring the beautiful parks, or taking a scenic bike ride along the river. In addition to its natural attractions, Portland offers a diverse culinary scene with a wide range of restaurants and food carts to satisfy any craving. The vibrant art and music scene also come alive in the summer, with numerous festivals and events to enjoy. With so much to offer, it’s definitely worth taking the time to explore and discover the hidden gems of Portland during the summer months.

A few places to stroll between eating, drinking, and laughing: Eastern Promenade, Mill Brook Preserve South Trailhead, Bug Light Park, and Portland Head Light.

Maine Mall

We started our weekend at the Mall. The birthday girl wanted to find a club fit. We weren’t successful in that endeavor, but I did manage to read a few pages in a book while I waited. Good thing Autumn brought a backup fit. The mall is a maze for me because I rarely visit, but Autumn seems to know exactly where she needs to go. We visited just a few stores before meeting her sister and sister’s man for an escape room.

Money Spent:

$10 pretzel bites

Maine Escape Room

Autumn and I enjoy escape rooms a lot. She’s only done one with me, but we’re pretty much professionals. Well, in the sense that we get real close to finishing and the people running the shop let us finish. God bless!

On a previous Portland adventure, Autumn and I completed Dr. Gem’s Time Trap. We like that the puzzles revolve around symbols more than math. Math is not our forte. But there’s a good mix of puzzle types from symbols to word problems and riddles.

There were four of us on this endeavor. We handled Uncle Ned’s Cabin. It was pretty tricky at times, but still a lot of fun. There’s nothing like an escape room to force some bonding between people. I liked this room because it reversed the concept of an escape room. Normally, you are leaving a room. In this case, we were entering. Great room for double dates!

Money Spent: $0 (thanks, Autumn)

Round 1

Who doesn’t love an arcade? Autumn and I burned some time prior to dinner here. We enjoy the tower stacking game. I got to within one stack from winning! There are all sorts of games in here if you haven’t been. Go solo or with some friends. It’s easy to spend $50 or more. So be wary. But it’s such a fun place. I haven’t done bowling or karaoke here yet. The arcade captures my attention, but not as much as this woman. She’s playing Pac Man here on the big screen.

Money Spent:

$50

Great Lost Bear

Hi Tony! Tony was our greeter and I honestly forgot his name for about ten minutes when he sat us down. Then it all came back to me and I felt I was back at Farmington! Wow!

Autumn and I left the hotel with Welles the Uber driver from Paris. We spoke for the whole trip in French before he dropped us for supper. It was a very late supper for us at 9:20pm. My lady and I split nachos and a cheesesteak. She didn’t like her pomegranate margarita, but she’s also not a big fan of alcohol. I wasn’t a fan either, but I don’t let a drink go to waste. I drank Maine Beer Company’s Lunch. Always solid! This was a decent amount of food and not too much before dancing. Great Lost Bear has an inviting atmosphere and great staff.

Money Spent:

$53

Bubba’s Sulky Lounge

I’ve got no pictures of Bubba’s! We were too busy dancing to 90s and early 2000s hits! I paid a $10 cover charge and we both had one shot of a kamikaze. It was gross. Gross may be the wrong word. Strong? Let’s call it that. We also got water. After the drinks, we danced! And time flies when you’re dancing from one song to another. We danced for two hours before calling it quits.

I like that Bubba’s is a lounge, but it has three dance sections with light up floors. You could go before it got busy to check out the antiques and especially the lunchbox collection. But the real party starts a little later in the evening (10pm) and goes until 1am. I am a big fan of dancing. I’d say we burned off quite a few calories based on how sweaty we were. But it was also just hot with all the people there. There was a bachelor and a bachelorette party there. Congrats, kids!

Money Spent:

$26

Eighty 8 Donuts (x2)

Donuts! This place sells bite sized deliciousness! We may or may not have visited twice. Two different days as you can see…that makes it better, right? We split the sixpack! On Sunday, we bought Boston Creme donuts. The donuts are made to order and they were warm and tender. We bought and demolished the maple glazed donuts on Monday. Both times, the wait time was quick. Less than five minutes. It was $7 for the maple sixpack and $8 for the Boston Creme. They offer 30 donuts for $25 and Autumn is hoping to go for that next time when we have more help to eat them.

This was our top spot!

Money Spent:

$16 (donuts and a yucky iced coffee)

Old Port

Shops, restaurants, walking, oh my! When most people think of Portland, the Old Port is the first thing that comes to mind…or maybe the lighthouses? Anyhow! The Old Port is a section of Portland rich in history and culture. It spans from Federal Street to Commercial Street, and York Street to Franklin Street. You’ll find many of the best pubs in town here! Bonfire is one of my favorites for the free bacon at happy hour. But Gritty’s, Three Dollar Deweys, and Lincolns are other solid spots.

Autumn is a shopper. So we checked out plenty of stores along Federal, Fore, and Commercial streets. I like history. The cobblestone roads, despite the pain they cause, are neat. And I love the brick buildings. I like trying to spot construction dates and imagining what Portland looked like while it was being built. Come during the day for shopping. Come at night to party at the numerous pubs, clubs, and bars.

Money Spent:

$11 at a bookstore

Mini Golf

We were surprised with a mini golfing invitation from my reenacting friends. How do you say no? We drove the 45 minutes to Richmond. Moose Mountain Adventure Park offers mini golfing and some other kid-friendly activities like mining. This was a grand time to hang out with my friends outside of the hobby. Great place for dates, friends, or families.

Keith won, but I think I came in second! Not that it matters! We really just enjoyed each other’s company.

Money Spent:

$26

Kume – Topsham

A great way to follow up mini golfing is hibachi. Autumn and I had plans for Five Guys and an evening of relaxing. We split a chicken hibachi supper and it was the perfect portion so we could eat later too. Hibachi is a great time. I wish I could be close to all my friends, but we shout across the flat top and that works too! Our chef was entertaining and provided good attention to the two kids joining us and Autumn.

Money Spent:

0$ (Thanks, Autumn!)

The Escape Room

Autumn and I were walking a lot on Monday. We strolled all over the Old Port and well into some other areas. It was a lovely day. Eventually, we needed a bathroom break. We looked in a Walgreens, a 7-11, and a few other shops. No luck. Eventually, we passed another escape room. Autumn said, “Why not?” So we signed up to play The Butcher’s Basement. This room was tricky with many math problems and a word problem. But we did manage to escape with much help from the employee working there. Talk about an expensive bathroom break!

Afterward, we chatted with the employee. She mentioned her favorite room: The Blind Tiger Speakeasy. We were sold! And they offer 20% off when you buy a second game on the same day. I really liked the theme of this room and it was a lot of fun. Difficult at times, but that’s the whole point! We did manage to escape the speakeasy with time to spare. Autumn and I will hunt for more of these rooms in the future.

We enjoyed all of our escape rooms this weekend. Both locations allowed us additional time as we neared the end and they were super helpful along the way.

Money Spent:

$40 (I bought the second game)

Gritty’s

We had two objectives before our Portland adventure concluded: lunch and ice cream. We happened to be walking Fore Street and spotted Gritty’s. We were served a solid amount of food. Look at all these tater tots! I had the reuben and Autumn ordered the chili. Hers was a solid mix of meat and sauce. It tasted delicious. I enjoyed the reuben, but I think it could have had more sauerkraut and thousand island dressing. Still, it was ate and enjoyed.

Money Spent:

$50

Beal’s

We were so ready for ice cream that pictures were not taken. I got peanut butter ice cream with peanut butter sauce…yeah, I have a problem. We enjoyed our treats just outside along Wharf Street. The sun was just warm enough to be enjoyed thoroughly. This was a fantastic finish to our weekend: ice cream with someone you really care about on a warm summer day in Portland, Maine. Does it get any better?

Money Spent:

$0 (Thanks, Autumn!)

Unfortunately, all things must end. Our drive home was filled with conversations revolving around the activities and food we ate. In particular, Eighty 8 Donuts continued to come up. We’ll visit several places again, but donuts will come first.

Do you have any favorite spots in Portland?