20+ Ways to Celebrate Valentine’s Day in Portland, ME!

It’s that time of year again! Love is in the air, champagne is bubbling, and chocolate will be going on sale soon! Whether you’re in a relationship or single and ready to mingle Portland, Maine is a fantastic place to spend your Valentine’s Day. You could catch a performance or comedy show, treat yourself to a delicious specialty dinner, attend a masquerade ball, or just dance the night away. The opportunities are endless! Grab your SO or your buddies and get out there!


Allagash Brewing Company’s From Maine with Love is a Valentine’s week extravaganza! Events run from the 9th-14th and include a donation-based yoga session, a baking class, card making, a truffle making class, movie streaming, a calligraphy workshop, and more! All with delicious beer available! See their Facebook for all the details!

The Frozen Funk Skating Party in Deering Oaks Park will be from 5:30-8:30 pm! This event features music by WJZP 107.9, free skate rentals, food trucks, and raffles! This is an all-ages event!

Music and Performances 

Maine Craft Distilling will be hosting Invoke for a Whiskey Chamber Valentines from 6-7:30 pm! Sit back and enjoy this quartet’s engaging, eclectic setlist. Plus, hors d’oeuvres and cocktail pairings will be available! 

“South Pacific” on the Tophat Miniature Stage at Mayo Street Arts is back this Valentine’s Day and on February 15th! This is a one-man, many figurines show. Along with his action figure cast, David Worobec sings and acts out every character in “South Pacific”. Doors open at 6:30 and the show starts at 7 pm. 

Urban Farm Fermentory is hosting Ladies of Love – Valentine’s Day Drag Show from 8-10 pm! Love songs and hate songs are on the menu so bring your SO or fly solo! The night is hosted by the amazing Cherry Lemonade. This event is 21+ and there’s a $5 cover. 

Snag a ticket, or two, for the Gina and the Red Eye Flight Crew Valentines Ball at Portland House of Music and Events! The doors open at 8 pm and the music starts at 9 pm. Tickets are $10 in advance and $15 day of! This is a 21+ event.

Head to Seasons’ Valentine’s Party with Tickle at Seasons Grille Restaurant from 8 pm-1 am. Tickle will be playing from 9:15 pm-12:45 am. Tickets are just $10. 

Comedy Shows

If you’re in serious need of a laugh this Valentine’s Day stop in for Back Room @ Mathew’s in Mathew’s Pub from 7-10 pm! Tickets are $10 and space is limited so call to reserve your spot! See their Facebook page for more information.  

Keeley’s Banquet Center is hosting comedian Bob Marley for Valentine’s Day! The show is from 7:30-9 pm. There’s a full bar and easy parking. Reserve your seat ASAP!

The Portland Maine Comedy Festival pairs with The Fireside Inn and Suites to give you a Valentine’s Day Comedy Night from 8-11 pm! This event is raising money for The Lafayette Family Cancer Center. Tickets are $20 for one and $35 for two! This is a 21+ show. 

Dance Parties

Step into the past for 80’s Prom Night at EVO Rock + Fitness from 6-8 pm. 80’s music will be blaring all night, the dance floor will be full, and a prom-style photo booth will be available for souvenir photos! $12 day passes are available for those in costume. 

There also an 80’s Prom Night at The Portland Hunt and Alpine Club which benefits Planned Parenthood of Northern New England! From 8-11 pm dance to 80’s hits and sip on themed cocktails! 80’s prom attire encouraged! This is a 21+ event.

Grab your friends and head to Single AF Valentines Edition from 9 pm-1 am at The Whiskey Barrel. All are welcome, single or not. Color-coded cups will be available to tell you whether or not someone else is taken, looking for friends, looking for a dance, or single AF! 

Check out Bliss, a warehouse dance party featuring multiple rooms of live performance art and DJs! Early bird tickets are $10-$15 and general admission is $20. Costumes are encouraged! See their Facebook page for more information.  

Fanciful Festivities

Attend the Masquerade @ The Mansion from 9 pm-1 am. This is a formal event so dress to impress. Masks will be provided at the door! Tickets begin at $30. This is a 21+ event.

Get to Plague and attend Laird Maxwell’s Speakeasy 30th Birthday Valentines Day hosted by Gothic Maine from 9 pm-1 am. 1920s attire encouraged! There will be cocktails available, DJs spinning gothic 20s music, and a performance by Laird Maxwell himself at 10:30 pm! Cover is $3 before 9:30 and $5 after. This is a 21+ event. 

Food and Wine

Old Port Spirits and Cigars will be hosting an Omen and Bliss tasting with Crush from 4-6 pm! Why not wine a little? 

Petite Jaqueline will be featuring a special menu for Valentine’s Day. They have tables open for reservation. Check out their Facebook page for a menu preview.

Vinland is giving a special six-course meal with the option for delicious wine pairings for Valentine’s Day 2020! There are two seatings, at 5:30 pm and 8:30 pm! All food is organic, gluten-free, and delicious!

Get tickets to Cellardoor Winery at The Point’s Valentine’s Dinner from 6-8 pm. This event pairs a delectable dinner by Natalia Dyer of Sampa Kitchen-Grillin’ Brazilian and amazing Cellardoor wines. Early reservations are encouraged as tickets go fast. See their Facebook page for more information. 

Attend a Titanic Themed Mystery Dinner Theater at Stroudwater Distillery. The event is hosted by Mystery 207 and catered by Locally Sauced! Tickets are $75.