Whether you’re planning a romantic night out, a Galentine’s celebration with your besties, a family-friendly outing, or something a little off the beaten path, Annapolis is bringing the love this Valentine’s season. From chocolate crawls and candlelit concerts to kids’ dances and creative workshops, here’s your guide to all the Valentine’s (and Galentine’s) events happening around town.
For the Crafty & Creative
Succulents & Sweethearts: A Valentine’s Day Workshop
February 12 | 11 AM to Noon | $50
Create a living Valentine that lasts. In this hands-on workshop, you’ll plant colorful succulents in a heart-shaped ceramic planter with step-by-step guidance along the way. Perfect for date night, a friends’ outing, or a thoughtful handmade gift. No experience required!
Homestead Gardens (Davidsonville)
Books & Bouquets
February 12 | 5:30 to 8 PM | $10–$30
This relaxed, after-hours shopping event pairs books and blooms for the ultimate Valentine’s gift combo. Browse a curated book selection, explore the greenhouse, and build a gift-ready pairing—no workshop or class, just easy browsing.
Homestead Gardens (Severna Park)
My Upcycled Valentine!
February 14 | 11 AM to 2 PM | $22–$25
Drop in anytime to create a meaningful, eco-friendly Valentine. Write a heartfelt note using a traditional quill pen on handmade paper, snap a photo at the selfie wall, and craft a keepsake card using upcycled materials.
Historic London Town & Gardens
For the Foodies & Shoppers
Annapolis Chocolate Crawl
February 12 | 3 to 7 PM
Sip, snack, shop, and swoon your way through downtown Annapolis. Participating boutiques will offer Valentine-themed treats, including chocolates, bubbly, and sweet surprises. Bonus: mention the Chocolate Crawl for 10% off at each stop.
Galentine’s Sip & Shop
February 12 | 6 to 8 PM
Grab your girlfriends and make a night of it. Shop at BD Provisions, Stella Luna Raine, Mezzanote, and Neighborhood Barre Severna Park for a chance to win prizes and score a Valentine’s gift bag when you visit all four. There will be vendors, hair tinsel, and plenty of festive fun.
Federal House Bar & Grille Valentine’s Weekend
February 13–15
Enjoy a romantic three-course dinner with wine pairing, followed by late-night dancing on Friday and Saturday night. A classic Valentine’s date-night option right in the heart of downtown.
Valentine’s Day at Rams Head Tavern
February 14 | 4 to 11 PM
Settle in for a relaxed and romantic Valentine’s Day dinner at Rams Head Tavern. Enjoy special dinner and drink offerings alongside live music from Scott Voorhees for an evening that’s cozy and festive. Reservations are recommended.
Rams Head Tavern
For the Romantics (and Music Lovers)
Love Stories to Tell in the Dark
February 12 | 7 to 10 PM | $5
Local authors take the stage at Cult Classic Brewing to share short love stories, each just 3-5 minutes long. You’ll experience romance, vulnerability, and stories that just might restore your faith in love.
Cult Classic Brewing
Momentum: A Mixed Bill
February 13 | 7:30 PM
February 14 | 7 PM
Celebrate Valentine’s Day weekend with an unforgettable night at the ballet. Hosted by the Ballet Theatre of Maryland, Momentum blends classical and contemporary works into a romantic, high-energy performance featuring world-premiere choreography. This mixed bill highlights bold new creations from emerging artists alongside innovative works by established choreographers, resulting in an evening that’s passionate and full of movement.
Maryland Hall
Candlelight: Valentine’s Day Special
February 15 | 6:30 to 7:30 PM | $37–$72
Experience a magical candlelit concert at Maryland Hall featuring a Valentine’s-themed musical program. A multi-sensory evening that’s equal parts romantic and unforgettable.
Maryland Hall
Emmaline: Be My Valentine Tour
February 15 | 8 to 10 PM
Jazz-pop vocalist and violinist Emmaline returns for a candlelit Valentine’s weekend concert filled with romance, roses, and a brand-new setlist. Doors open at 7 PM.
Rams Head On Stage
For Families & Kids
Pre-K Art Party: Valentine’s Day
February 13 | 10:30 to 11:30 AM | Free
Little ones are invited to explore Valentine’s-themed process art. This event promises to be hands-on, messy, and fun. Wear clothes you don’t mind getting creative in.
Discoveries at Annapolis Mall Library
Sweetheart Dance
February 13 | 7 to 9 PM | $10
A family-friendly Valentine’s celebration for parents, caregivers, and kids. Dress up, dance, and make memories together.
Pip Moyer Recreation Center
For the Fitness Girlies (and Guys)
Annapolis Striders’ Valentine’s 5K
February 21 | 10 AM to Noon
This low-key, beginner-friendly 5K welcomes runners of all ages and abilities for a scenic 3.1-mile loop on paved paths at Kinder Farm Park. A great way to celebrate for those who love running or just being outside.
No matter how you’re celebrating this Valentine’s season, romantic, platonic, family-style, or solo, Annapolis has something sweet planned. Mark your calendar, grab your people (or treat yourself), and lean into all the ways love shows up around town this February.
Super Bowl Takeout Specials