Caiola's Portland Maine

In our last post about Caiola’s, where we covered their delicious Sunday brunch (hopefully, you’ve had the chance to try the Lost Bread since then), I mentioned that there are few better ways to spend a warm summer evening than on the back patio of this West End favorite, surrounded by good friends, great music, and fantastic food. Recently, we had the opportunity to do just that, and I’ll have to admit that it turned out to be an even better time than I had originally billed.

Every Thursday night, Flight of Fancy, an all-string trio (two-thirds of which are our good friends Darcy & Carolyn), wows patrons with its amazing melodies from the back patio of Caiola’s. They claim that they are merely playing background music for you to enjoy with your dinner, but it’s a rare evening when they don’t win over and silence the crowd with their songs. We took advantage of the chance to hear Flight of Fancy play over a good meal, with a couple of friends from our neighborhood, and made reservations for the patio.

After some brief hellos and introductions, we placed an order for drinks (sangrias, Peeper, and Geary’s HSA) and starters (the delicious Polenta Fries and the Steak Bruschetta). With Flight of Fancy in the background, we devoured the appetizers and moved on to bigger things. The four of us enjoyed the Chicken Marsala (with Roasted Shallots, Mushrooms and Tomato Tubettini), the House Made Cannelloni (with Ricotta, Sweet Peppers and Spinach in a Tomato Sauce with Parmesan), and two Caiola’s burgers. The Caiola’s burger is sometimes easy to overlook as the last item on a menu stocked with tempting choices, but once you’ve had one of these juicy creations with bacon, cheddar cheese, and a few large mashed potato tator tots (they will absolutely leave you speechless), you’ll find that your eyes begin to drop to the bottom of the menu from the get-go on subsequent visits.

Somehow, we polished our plates, relaxed with some fun conversation and sensational music, and then made room for one of Mere and my favorite desserts – the Panna Cotta. It’s hard to share such a tasty delight, but we managed to part ways with a few bites, and spent the rest of the evening laughing and listening before we crossed back over the bridge and called it a night.

Caiola's Menu

Caiola's Patio


Bruschetta at Caiola's

Polenta Fries

Flight of Fancy

Caiola's Cannelloni

Caiola's Burger

Caiola's Panna Cotta

Caiola's Dessert

Map and Menu

3 thoughts on “Caiola’s

  1. One of the best nights this summer! Beautiful people, delicious food & conversation… It wasn’t work at all!! Thrilled that our music was a part if it!

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