5 Fun (and Cheap) Portland, Maine Summertime Dates



Every year around this time, a funny thing happens in Portland, Maine. As the extra pounds of cold weather snacking melt away, the bulky layers of clothing disappear, as well. Freckled faces and bronzed, nearly bare bodies, come out of the woodwork and slowly fill the bars, restaurants, and shops of town. Maybe it’s the temperature, or the crisp summer ales on tap, or perhaps it’s the skimpier attire, but something happens to Mainers in the summer. Suddenly, everyone is much more down to…date? Yeah, down to date. That’s the saying on Jersey Shore, right? DTD.

So, let’s say you’re out and about somewhere in Portland and you encounter someone cool enough to take out and “date” the crap out of. You’re all tingly and smiley and all that bologna. But, oh no! Your job sucks and your bank account is nothing short of embarrassing. You should definitely give up on dating all together. Cash in your dreams of DTD and surrender to the fate of DTPVGAIYPB (Down To Play Video Games Alone In Your Parents’ Basement).

No, wait. Don’t do that. That’s embarrassing. I feel bad if that’s your reality. I’ve dated (probably too many) broke men. And my obsession with going out to eat has pretty much destroyed my credit. So I know what’s good when you’re trying to have fun on the cheap. How about I share some of my favorite thrifty summertime dates? Here goes:

1. MENSK Rooftop Film Series

Normally I’d say don’t take someone to the movies on the first date. You can’t talk. It’s dark. The seats are often uncomfortable. And there’s that whole awkward “who’s going to pay?” question. And if you’re broke, you probably don’t even want to pay for your own ticket, let alone someone else’s. But I’ll bet a pretty penny you do want to get some…hand holding, or whatever the kids are doing these days. Dilemmas, dilemmas.

Well, rest easy: this rooftop series is kind of the perfect solution. It’s outside on the rooftop of the Spring Street Garage so you aren’t missing a fabulous summer night in Maine. It’s free so that pressure of taking charge financially is gone. And you bring your own seating so your buns will be at peace. Also, everyone knows movie snacks are a rip-off. I almost always sneak them in (except on bargain Tuesdays at The Nick because they only charge $5 for movies and I feel bad being a sneak then). But, at these rooftop screenings, you’re more than welcome to bring your own snacks. Look at you, saving money and still having fun. The movies are screened around sunset every third Sunday throughout the summer. Click here for this season’s line-up.

Tip: Take your date to see Up on July 15. You’ll laugh. You’ll cry. After that emotional rollercoaster, your date is bound to feel more vulnerable than usual.

2. Millcreek Park Concert Series

Since it’s not exactly tropical in this state, you really ought to take advantage of the beautiful summer weather, brief as it may be. So this “date” is another outdoor event. Millcreek Park is right over the Casco Bay Bridge (or the Million Dollar Bridge, if you are old enough to remember that). It’s not six minutes from Portland. Like the rooftop series, these Wednesday evening concerts held here are free. It’s a great way to check out local talent (like The Mallet Brothers Band) and since these shows go down at 6:30pm, right around suppah time, you can bring a picnic and get real date-like and romantic about it, if that’s your style. For a schedule of this year’s concerts, click here.

3. Sunset Folk Series on the Western Promenade

If you’re really broke, you may not even have gas money to get over the Casco Bay Bridge into South Portland. Again, don’t give up. You can still enjoy some free music in a lovely Maine park. If you live in Portland, you can hoof on over to the Western Promenade for the Sunset Folk Series, also on Wednesday evenings. These concerts are sponsored by Families of the Western Prom Neighborhood, and as evidenced by the name of the series, they happen around sunset. The concerts are typically around 40 minutes, so perhaps spend the rest of the evening walking about town. If you get hungry, maybe check out some of these late-night food stops.

*If you don’t live near the Western Prom, but are located in Portland, here are a few more free outdoor summer concerts.

Kurt Baker at the Sunset Folk Concert Series

4. Go Bike Riding!

Remember when you were 12 and you’d call up your friends and ask the age-old “wanna ride bikes” question? Adults should ask that question to each other more often (I use the term “adult” lightly). While Portland is a very bike-friendly city, some people think you have to be hardcore into biking to take advantage of the trails. I am probably the least athletic person in New England but sometimes there’s nothing quite like hopping on your bike. And if the person you are interested in owns a bike, too, well then heck, why not get together for a good old-fashioned bike ride. There are a bunch of Portland-area trails if you want to stick around town. But if it’s a really nice day, consider riding to one of these beaches. You won’t have to pay for parking if you cruise in on bikes.

5. Happy Hour

Not everyone’s a drinker, and I’m by no means advocating you drink to lose your inhibitions on this proposed date. However, if you like to imbibe but aren’t fond of spending a ton of money, happy hours in Porland are clearly the places to be and can serve as a perfect opportunity to get to know someone better. Some of my favorites include (but are not limited to) the following:

Shay’s Pub Grill–With drink and food specials Mon-Sat and located right in the heart of Monument Square, this is the perfect place to grab a beverage and people watch. My favorite night of the week is Thursday: Talls for Smalls are fabulous when I’m in a beer mood and their house wines are just $3 from 4pm to close.

Pai Men Miyake–They’ve got a lovely little patio overlooking Longfellow Square. And they boast not one, but two happy hours for your money saving pleasure. First one is from 4pm-6pm and the second one goes down 10pm-midnight. Their new peach ginger sangria is delightful, especially on a hot summer day, and it’s just $4 for a glass during both happy hours.

Great Lost Bear–OK. Tehcnically, this isn’t a “happy hour” special, but on Monday and Tuesday nights the Bear features Talls for Smalls. And with about six zillion beers on tap (perhaps a slight exaggeration), it’s the perfect place to take advantage of such a steal. So if your special someone is a beer person, this is your place. Don’t want a Tall? That’s cool. Every week they have a featured regular sized pint for just $2.99.

All right kiddos. Those are my picks, for now.

Don’t want to go on a date to get some…hand holding? Fair enough. Try going to Wharf Street on any given weekend night. No romantic bike rides necessary to get your “hand held” with that crowd. I jest, I jest…kind of.

Drop some knowledge.