Imagine strolling through the charming, historic streets of downtown Annapolis, Maryland, with a glass of sparkling wine in one hand and a rich chocolate bite in the other. Annapolis is famous for its colonial architecture and beautiful harbor. During the Annapolis Chocolate Crawl in February, small shops and boutiques in this beautiful city turn it into a candy lover’s dream.
People of all ages are welcome to stroll from shop to shop on Thursday, February 12, 2026, and enjoy gourmet chocolates, Valentine-themed drinks, and handmade treats while learning about interesting local businesses.
There is more to the Chocolate Crawl than just tastings. It captures the love mood before Valentine’s Day and turns a normal afternoon into a delicious mix of exploring and indulging. There will be sweet treats and special deals at shops, making it one of the tastiest ways to celebrate love, friendship, and the city’s strong community.
Let’s get deep insights of things to do in Annapolis Chocolate Crawl 2026 with Zavros Place!
Essential Event Details
Date & Time
The 2026 Annapolis Chocolate Crawl will take place on Thursday, February 12, 2026, from 3:00 PM to 7:00 PM. From mid-afternoon to early evening, this is a great time for a fun date, a trip with friends, or a slow walk through downtown Annapolis.
Location
The event takes place all over old downtown Annapolis. Many of the shops that are taking part are located on Main Street and nearby blocks. Most of the samples and discounts start around 155 Main Street, but the crawl usually goes to a few different shops and boutiques that are close enough to walk to.
Admission & Participation
The Chocolate Crawl is usually free to enter; you do not need to buy a ticket ahead of time unless some shops add special events that require tickets. People can just walk from one shop to the next, try free samples of chocolate, and enjoy the holiday activities all over downtown.
Special Perks & Discounts
People love the “secret phrase” part of the event: if you say “Annapolis Chocolate Crawl” at shops that are taking part, you can often get a 10% discount on purchases made during the event. Along with their products, many shops serve special drinks and snacks.
Where to Eat & Drink: Your 2026 Schedule
The Chocolate Crawl route goes through some of the most beautiful blocks in Annapolis’s historic downtown district, whether you have lived there your whole life or are just coming for the first time. The majority of stops are located near Main Street and nearby side streets. Each shop that is taking part pairs seasonal treats with Valentine’s Day-themed treats.
Organizer Hub — The Spice & Tea Exchange (155 Main Street)
Start your tour at Annapolis’ Spice & Tea Exchange, the event’s hub. This shop is known for its colorful selection of handmade teas, spice blends, and seasonal drink mixes. During the crawl, they often have chocolate-infused tea samples and treats with sugar on the edges. There are warm cocoa blends and personalized infusions that would make great gifts or keepsakes.
Main Street Boutiques — Sip, Shop & Stroll
Main Street is the crawl’s hub, with fashion, gift, and specialized boutiques offering sweets and nibbles:
- Seasons Olive Oil & Vinegar: Serve dark chocolate samples with balsamic drizzles and olive oil flights.
- Local Coast Apparel: This boutique combines seaside style with holiday charm, and they might have fizzy prosecco samples and candy chocolates.
- Brightside Boutique & Lucky Knott: Additionally, Brightside Boutique and Lucky Knott are stylish gift shops that serve handmade hot chocolate, truffles, and other sweet treats to keep you going as you explore.
You can get Valentine-themed drinks at these stops, like prosecco, chocolate martinis, and rich, slowly mixed hot cocoa, which are great for drinking while you browse.
Maryland Avenue & Historic Side Streets — Hidden Gems
Check out Maryland Avenue’s quieter length and Main Street’s side lanes. Here, a number of local artists and specialty food makers sell candies and sweets that they make by hand:
- Woodcraft Artisans: Here you can find both handmade woodworking and local sweet treats. Try the small-batch truffles or chocolate-covered pretzels.
- Kim Hovel and The Cottage Shops: These are charming historic shops that often have hand-picked chocolates, Valentine’s Day decorations, and unique gifts.
- Zachary’s Jewelry & Gifts: This is not a food stop, but it is a great place to find thoughtful gifts to go with your sweet crawl, and you might even get chocolate samples from local partners.
Enjoy the crawl’s historic atmosphere amid tree-lined streets and traditional Annapolis architecture in this quieter neighborhood, perfect for sweets and taking pictures.
Swoon Worthy Bites & Sweet Surprises
During the crawl, keep an eye out for pop-ups and other treats:
- Truffle Tastings: Many shops sell hand-made truffles that pair with unique flavors, such as sea salt caramel, raspberry ganache, or bourbon pecan.
- Chocolate Covered Pretzels & Confections: Salty and sweet snacks to eat while you walk.
- Bubbly Pairings: Several stops offer short samples of sparkling rosé and prosecco that go well with stronger chocolate flavors.
Shopping with a Sweet Twist
The Annapolis Chocolate Crawl is not just a chance to enjoy chocolate; it is also a great chance to support local businesses, find unique gifts, and stroll around lovely downtown Annapolis.
Maximize the 10% Discount Rule
A lot of stores on Main Street and Maryland Avenue will give you a 10% discount on normal items if you say the Chocolate Crawl secret phrase, like “Annapolis Chocolate Crawl.” To get the most out of this:
- Verify from each store to see if they are giving the discount; it varies from store to store.
- Plan your purchases around jewelry, small handmade items, Valentine’s Day gifts, or holiday decorations.
- Do not go down the same streets more than once. Instead, combine your stops for treats with gift shopping.
Featured Gift Ideas in Downtown Annapolis
There are almost 90 shops in downtown Annapolis that all have unique items that would make great Valentine’s Day or holiday gifts.
- Boutiques like Whimsicality and The Cottage that sell jewelry, trinkets, and small gifts.
- There are gift and specialty shops that sell local goods, decorations, and souvenirs with a nautical theme.
- Annebeth’s on Maryland Avenue is famous for its boxes of Maryland favorites, which are great for stocking with crawl goodies.
Supporting Local Businesses
Every sale goes straight to the small shops and entrepreneurs that make Annapolis what it is. Your support helps keep employment open all year, brings attention to local artists, and keeps this historic downtown alive, even after the Chocolate Crawl is over.
Expert Tips for the Best Experience
A little planning goes a long way toward making the Annapolis Chocolate Crawl stress-free and fun, whether you are a first-time visitor or a local planning your annual chocolate adventure.
Dress for Comfort & Weather
Comfy shoes are essential: You should wear comfortable shoes because many of the streets in ancient Annapolis are cobblestoned, which can be rough and make walking for long periods tiring.
- In February, Maryland might be cold and windy, so wear thick apparel between stops.
- Gloves, a cozy scarf, and a weather resistant coat will keep you comfortable as you sip and stroll downtown.
Go Early & Avoid the Rush
- Arriving near 3:00 PM when it starts helps you beat the early evening crowd that builds closer to 5:00 PM.
- Starting earlier also gives you more time to explore boutiques and treats before stores get crowded.
Stay Hydrated Throughout
- It is easy to forget to drink water with all the free chocolate, drinks, and hot cocoa.
- Bring a small water bottle with you and sip from it between tastings. This will help you enjoy stronger flavors more and keep you hydrated.
Parking & Transit Pro Tips
- The Gotts Court Garage is one of the best places to park and walk close to downtown Annapolis.
- The Whitmore Garage is just one block away on Clay Street and has plenty of parking spots. It is also only a short walk from the crawl area.
Other city garages or lots and the free Circulator bus, which loops between downtown parking locations and shopping districts, are cheaper alternatives to central parking.
Beyond the Crawl: Make It a Date Night
Add dinner, sunset views, and charming local lodging to the Annapolis Chocolate Crawl for a romantic evening or mini staycation.
Dinner Reservation Ideas — Romantic & Delicious
After you have tried the chocolates and walked along the old streets:
- Osteria 177: It is a great place for a special night out because it has classic Italian food, wine, and a classy atmosphere right on Main Street.
- Carrol’s Creek Cafe: Many people consider this to be one of Annapolis’s most romantic restaurants because it is right on the water and serves seafood from the Chesapeake Bay.
- Vin 909: Is a wine café with creative American food and a cozy space, great for dinner.
- Dock Street Bar & Grill: If you want a fun meal before the sun sets, Dock Street Bar & Grill is a great pick.
Sunset at City Dock
Walk leisurely to City Dock after dinner to watch the sunset and see Spa Creek and the Annapolis waterfront. Locals and tourists adore walking near the waterfront and capturing sunset shots.
Staycation Options — Historic & Charming
These historic inns and B&Bs are at walking distance from the crawl for overnight or weekend stays:
- The Historic Inns of Annapolis are a group of beautiful old houses right in the middle of downtown.
- Gibson’s Inn At Gate One is a charming boutique hotel just from Main Street and City Dock.
- Flag House Inn or Chez Amis Bed & Breakfast, cozy B&B options for couples seeking a quieter getaway downtown.
- Walking distance to restaurants, attractions, and rivers, these ancient inns are perfect for a romantic night after your chocolate trip.
Conclusion
The Annapolis Chocolate Crawl is a February event worth attending for its delicious treats, historic charm, and small town romance. At this fun event, drink, munch, stroll and shop in Maryland’s capital with friends, family, or a special one.
This 2026 chocolate crawl celebrates love, local craftsmanship, and downtown Annapolis’ strong community spirit with festive boutique goodies, gorgeous photo possibilities, and waterfront sunsets. Enjoy the city’s sweeter side and develop memories that stay long after the final chocolate bite.