Celebrate Valentine’s Day in downtown Cumberland!
Valentine’s Day is something special for lovebirds of any and all ages.
So, make your reservations at historic city center restaurants now and follow our Facebook page at Cumberland Alive as good ideas are added!
Something SWEET is coming to Messick Road!
We are so excited to welcome you to our newest branch, and we’ve got a delicious way to celebrate! Starting February 11th through Valentine’s Day (Feb 14th), we’re giving away custom Chessie Chocolate Bars to say “thank you” for being a member!
Where: Exclusively at the new Messick Road Branch
When: Feb 11th – Feb 14th
Who: The first 300 members to stop by!
Come check out our newest space, meet our friendly team, and grab a treat while supplies last. We can’t wait to see you there!
Saturday, February 7, 2026 • 1:00 PM – 4:00 PM
50 N. Centre Street
Grab your favorites and enjoy an afternoon with us!
Join us for our Galentine’s Event at Myla + Maple – the perfect excuse to gather your girls and treat yourself.
• Botox
• Rosé bar
• Live DJ & more
Sunday, February 8, 2026 • 12:00 PM – 4:00 PM
118 Baltimore Street
Grab your girls and get ready for the ultimate Gal Pal party!
Join us Sunday, February 8th at Madison Paige Boutique for a day full of shopping, sipping, and fun!
Bring your besties, wear pink, and make it a day to remember!
Plus more surprises in store!
A Valentine’s Weekend Foster Campaign
716 Furnace St Cumberland, MD 21502 • info@ashelterofhope.com
Looking for a Valentine’s date with zero drama and all the cuddles? We’ve got you.
Valentine’s weekend, your perfect companion will have four paws, a wagging tail, and the kind of love you can’t swipe past.
Foster a dog for Valentine’s weekend!
We’ll send you home with a “Weekend Companion” (aka your date!). Enjoy the snuggles, the laughs, and the unconditional love
BUT HERE’S THE CATCH… We pick your match.
That’s right, we’re the matchmakers! We’ll pair you with a pup whose personality fits your home and vibe.
FELL IN LOVE? If you “match” with your Weekend Companion and decide to adopt, your adoption fee will be just $75!
Ready to be matched? Message us or stop by the shelter to sign up for No Strings Attached!
Love might be unpredictable… but this kind is the best kind.
82 Baltimore Street • 301-724-1711
Join us for Valentine’s Day! We are an easy going pub that has been a downtown tradition for over 25 years.
Reservations recommended. Click below to see our menu.
Heartbreak Hotel!
101 N. Johnson Street • 301-759-4990 • cumberlandtheatre.com
MARK YOUR CALENDARS! THE KING OF ROCK AND ROLL IS CHECKING INTO CUMBERLAND THEATRE!
Vacancies are going quickly, so grab your tickets now!
Show Dates: January 27th – February 15th
Friday and Saturday Engagements: Doors at 7:30 pm and Show at 8:00 pm
Sunday Matinees: Doors at 1:30 pm and Show at 2:00 pm
We can’t wait to show you our moves!
49 Baltimore Street • 240-362-7183
Embassy Theatre proudly presents its 2026 Season opener, Checkmate, an original play by Sawyer Jenkins, Friday, February 13 and Saturday, February 14, 8 pm; Sunday, February 15, 2 pm.
Tickets are $15 and may be purchased on our new website – https://onthestage.tickets/show/embassy-theatre-corporation/69607 or at the door.
Todd Shultz has been arrested for the murder of his girlfriend, Kelly. For five straight hours, detectives Barney and Judy have been harassing, manipulating, and interrogating Todd. Throughout this story, Todd is being painted as a terrible man as he tries in every fiber of his being to claim his innocence.
This production is considered Rated R. It contains adult language, violence, guns, flashing lights, and sensitive topics.
Friday, February 13 • 5 – 8 PM
157 Baltimore St., 3rd Floor
Got an ex? We’ve got axes.
Join us for EXES & AXES — our Anti-Valentine’s Event at Fore Axes!
• Music by DJ Racos
• Show a text from your ex = $5 OFF axe throwing
• Drink specials + Hate-Throw Happy Hour
Saturday, February 14 • 5 – 9 PM
157 Baltimore St., 3rd Floor
STRANGE LOVE THINGS This Valentine’s Night, things are getting a little… strange.
Upside Down Hour (Happy Hour) starts at 5PM
• Singles & couples discounts on drinks + axe throwing
• Live 80’s-themed line dancing with DJ Racos & Melissa 7–9PM
• Valentine’s After Party kicks off at 9PM
Love it. Hate it. Throw an axe about it..
Saturday, February 14 • 10:00 AM – 5:00 PM
Fort Cumberland Emporium • 55 Baltimore Street
At Fort Cumberland Emporium we love our customers! Just for you, we’re having a Hearts Afire Scavenger Hunt. We’re hiding hearts throughout the store; find one and get a prize.
There’ll be some sweet treats, too
Rhinestones & Rust
Saturday, February 14, 2026 • 7:00 PM – 9:00 PM
Gallery Stage, 9 N. Centre Street • 301-268-3971 • www.gallerystage.com
Celebrate Valentine’s Day with an unforgettable evening of fine dining and live music at Gallery Stage! Enjoy a gourmet buffet dinner at 6 PM, followed by a 7 PM performance from Nashville duo Rhinestones & Rust — known for their captivating blend of classic and contemporary country.
$75 per person (dinner + concert, plus tax)
Limited seating. Advance tickets only.
Treat someone special to great food, great music, and a warm, art-filled atmosphere.
We can’t wait to celebrate with you!
Saturday, February 14, 2026 • 8:00 PM – 9:30 PM
Loft 129, 129 Baltimore Street • 301-268-3971 • www.loft129.org
FLOAT LOAF COMEDY presents Stand-Up Comedy @ The Loft! Saturday, February 14, 8 – 9:30 pm
“I love being married. It’s so great to find one special person you want to annoy for the rest of your life.” — Rita Rudner
Back again for Valentine’s Day – come yuck it up with the apple of your eye with another great line-up of the East Coast’s best comics! This show features five fantastic comedians, including headliner Lisa Chimenti and featured comedians Lennon Free, Corey Bush, and Clarilee. The Show is hosted by local favorite Tate Griffen. Tickets only $15
127 Baltimore Street • 443-548-1405
Valentine’s Date Night at Lily Books
Saturday, February 14th • 5:00 pm – 10:00 pm
Come for specialty coffee drinks and desserts. Hang out with your sweetie at Lily Books.
Lily Roundtables: Book Talk – Romance!
Sunday, February 15th • 4:00 pm – 5:30 pm
Join Romance aficionado Theresa Vernot and get into the spirit of Valentine’s weekend with a lively discussion of romance novels. Bring your favorite to share.
Saturday, February 14, 2026 • 5:00 PM – 8:00 PM
48 N Centre Street • 240-362-7950 • madhatterboba.com
Love is in the air!!!
Join us for Valentine’s Day Dinner at Mad Hatter’s with dinner specials including; Lollipop Lamb Chops
Baked Oysters
New love potion: “Mad About You”
Grapefruit & strawberry liquor w a slash of Sprite, garnished w/ fruit & golden sugar
…and special guest appearance by Black Magic Circus
13 Canal Street • 301-759-4400 • wmsr.com
Our special Valentine’s Day Dinner Train returns Friday, February 13th, featuring an exclusive Surf & Turf menu with filet mignon and lobster tail, alongside Tuscan chicken, pan-seared salmon, and a vegetarian option.
The February 13th train is your best opportunity to book, as space on our February 14th Valentine’s Day trip is now becoming very limited.
Celebrate Valentine’s Day aboard the Western Maryland Scenic Railroad with fine dining, romantic views, and an unforgettable evening on the rails.