Downtown Baltimore turns into a vibrant hub of romance, fun and unforgettable experiences on Valentine’s Day. Whether you’re planning an active morning, a cultured evening, or a fun night out, you have options on and around February 14.
Cupid’s Chase 5K – Morning Run for Love
Kick off Valentine’s Day with heart-pumping fun at the Cupid’s Chase 5K. This is a certified 5K run/walk that invites runners, walkers, strollers and even leashed pets — perfect for couples, friends, or anyone looking to start the day with energy and purpose.
The race begins at 10:00 AM (check-in starts at 9) at West Shore Park. The route follows the Inner Harbor – where there are lots of places to stop afterwards for a post-run brunch.
Race fees help support Community Options, Inc., a nonprofit focused on empowering people with disabilities.
Cupid’s Takeover Party at Power Plant Live! – An All-Night Valentine’s Celebration
Spend Valentine’s evening at Power Plant Live!, the heart of Downtown Baltimore’s nightlife scene, for Cupid’s Takeover — a lively, multi-venue Valentine’s celebration starting around 7:00 PM on February 14.
This event transforms the Power Plant Live! district into a high-energy Valentine’s playground with:
Mosaic’s Heated Rivalry — dance, drinks, and fun vibes.
Luckie’s Tavern — Girl Dinner experience with karaoke.
Leinie’s Garden Party — cupcakes, spritzes, and espresso cocktails.
Angels Rock Bar — Pop Princess party and Shred Your Ex moments.
PBR Stop Light Party — show your status with beads and enjoy themed drinks.
Cupid’s Takeover is designed for ages 21+ and offers something for everyone — whether you’re out with your partner or enjoying a group night with friends.
For more information, visit our Power Plant Live! Events Page.
Romantic Dinner at The Capital Grille – Fine Dining by the Inner Harbor
Make your Valentine’s Day dinner truly special with a reservation at The Capital Grille — an upscale steakhouse right in the heart of Baltimore’s Inner Harbor.
Known for its expertly dry-aged steaks, fresh seafood, award-winning wine list, and elegant atmosphere, it’s a classic pick for couples celebrating love and connection.
A few tips to make your night extra-special:
Make a rezzy: Reservations are highly recommended for February 14 — especially for prime dinner times in the evening (e.g., 7 PM).
Do something special: In some years the restaurant offers complimentary touches like chocolate or sparkling wine around Valentine’s Day — contact the restaurant directly to see what special offerings might be available for 2026.
A Date with John Waters – Show at Baltimore SoundStage
For entertainment with a twist, plan your night around “A Date with John Waters” at Baltimore SoundStage. This Valentine’s Day show brings Baltimore’s own iconic filmmaker and personality to the stage for an evening of quirky and raunchy humor and storytelling starting around 8:00 PM.
For tickets and more details, visit our Baltimore Soundstage Events Page.
Easy Parking Downtown
Planning ahead is romantic. When making your Valentine’s Day plans, don’t forget to have a good parking strategy in place. Located at 55 Market Place in downtown Baltimore, Harbor Park Garage is a short walk from all the best places and activities happening on Valentine’s Day. The garage is easy to access and convenient to major routes in and out of the city (including I-83) and parking spots can be prebooked, making your trip downtown even easier.
Baltimore Region: Beyond the Inner Harbor
Looking for more? Discover concerts, festivals, sports, and more happening throughout the region. Click here for the full list of upcoming events