The 8th Annual St. Michaels ChocolateFest is coming back in 2026, and it looks like it will be the tastiest day of the year on the Eastern Shore of Maryland! When it comes back on March 7, 2026, this popular event turns Historic St. Michaels, Maryland into a chocolate lover’s dream, with tempting samples, handmade products, and food with a local twist.
Unlike most food events, ChocolateFest turns the whole town into a stage for chocolate discovery. Bakeries, cafés, restaurants, and specialty shops all offer rich treats and creative dishes inspired by chocolate.
Whether you are walking along the waterfront or enjoying a sweet treat with a glass of wine, this event has something for people of all ages: new foods, community spirit, and holiday fun.
Find out about the dates, how the festival works, ticket choices, must-see places, travel tips, and frequently asked questions (FAQs) in this guide. This will help you plan the perfect chocolate-filled day in St. Michaels.
Are you ready to explore the fun and exciting things to do in Annapolis’ 8th Annual St. Michaels ChocolateFest with Zavros Place!
Event Details: Dates, Times, and Location
Date & Time
- The 8th Annual St. Michaels ChocolateFest will take place on March 7, 2026. It will be a sweet day full of chocolate tastings and sweet finds. As long as treats are still available, the Chocolate Crawl part of the event will go on from 11 a.m. to 4 p.m. in downtown St. Michaels.
- Events at ChocolateFest happen rain or shine, so plan to walk around the streets no matter what.
Location
- The event takes place in Historic St. Michaels, Maryland, a cute town on the Eastern Shore with a harbor. Talbot Street and nearby businesses that are taking part in the event are the center of it all. These include restaurants, bakeries, tasting rooms, and specialty shops.
- St. Michaels has historic buildings, a walkable center and stunning views of the Chesapeake Bay. These are what make it a beautiful venue of a food oriented event such as ChocolateFest.
What to Expect
People who go to ChocolateFest can look forward to:
- Chocolate tastings from bakers, chocolatiers, and restaurants in the area.
- Some places offer chocolate-themed food and drink pairings, such as wine and spirits.
- All over town, you can find handmade sweets, treats that make great gifts, and festival-only items.
How it Works: The Chocolate Crawl vs. Seated Tastings
There are two main ways to enjoy the tasty treats at the St. Michaels ChocolateFest: the Chocolate Crawl, which is more relaxed, and the Seated Tastings/Special Experiences, which are more formal. Each gives people a unique way to enjoy this yearly chocolate festival in Historic St. Michaels.
The Chocolate Crawl — Main Festival Experience
The Chocolate Crawl is the main event of ChocolateFest. It is a self-guided tasting tour that turns downtown St. Michaels’s streets into a strolling path of chocolate treats.
- When: March 7, 2026, 11 a.m. to 4 p.m. (or until samples run out).
- Where: All over town, mostly along Talbot Street and in the shops nearby.
- How it works:
- Just show up ready to explore, you do not need to buy a ticket ahead of time for the crawl itself.
- Go to businesses that are taking part and buy chocolate-themed treats and drinks.
- Pay for each taste and buy as you go. Most vendors will take small bills or credit cards.
This set-up makes the event adaptable and fun for everyone who comes. You can take your time, pick up treats from different places, and enjoy a chill, social space full of chocolate tastes.
Seated Tastings & Specialty Experiences (Optional Add Ons)
While the main crawl is more laid-back, during ChocolateFest weekend, a number of local sites and restaurants host more organized chocolate and wine tasting events. Among these experiences are often:
- Chocolate that goes well with beer, wine, or other drinks.
- Chocolate samples with expertly chosen choices.
- Sit-down events with hosted service and meals just for them.
These tastings require reservations because places are limited and prices vary by venue, unlike the Chocolate Crawl.
Quick Tips
- Start with the Chocolate Crawl to try a lot of different treats and get a feel for the event.
- To get a more refined or educational chocolate experience, make a reservation ahead of time for a taste while sitting down.
- Wear shoes that are easy to walk in and bring small bills with you to make sampling around town quick and fun.
Tickets and Pricing: Plan Your Budget
To plan your trip to the 8th Annual St. Michaels ChocolateFest on March 7, 2026, it helps to know how much it will cost and how much money you can spend on a day full of chocolate in Historic St. Michaels.
Chocolate Crawl — Pay As You Go
- You do not need to buy tickets ahead of time for the main event, the Chocolate Crawl, just show up and look around!
- Visitors to downtown St. Michaels can enjoy unique chocolate-inspired snacks and samples at participating stores, restaurants, bakeries, and tasting rooms.
- People can buy samples or items directly at each place in town, so it is easy to spend as little or as much as they want.
- It is easiest if you bring small bills like $1s and $5s to speed up the lines for samples, but many sellers also take cards.
Seated Tastings & Special Ticketed Events
- Besides the casual crawl, some places in the area hold special tasting events over ChocolateFest weekend that need tickets or reservations.
- For example, Simpatico Italy’s Finest provides wine and chocolate pairings at varying prices, such as 8 wine tastings + 5 chocolates for $15 or 16 tastings + 10 chocolates for $25.
- Most of the time, you have to book these seated or curated experiences ahead of time because space is limited and you only get certain things with your ticket.
Make it a Weekend: What to Do in St. Michaels MD in Winter
If you want to make a full weekend trip out of St. Michaels ChocolateFest, Historic St. Michaels, Maryland has lots to offer, even in the winter. There are museums, beautiful walks, cozy indoor activities, and cute local shops.
Explore Local Attractions & Museums
Chesapeake Bay Maritime Museum
One of the best things to do in St. Michaels is to visit this 18-acre waterfront museum. It has hands-on exhibits, traditional boats, old buildings, and history of the Chesapeake Bay. It is a great thing to do in the winter because the exhibits and activities are open all year.
Historic Sites & Walking Tours
As you walk around town, you can see famous sites like the Cannonball House, a well-preserved home from the early 1800s that is important historically because it was used in the War of 1812.
Shopping & Indoor Activities
- Talbot Street and downtown are full of shops, galleries, and gift shops where you can look at handmade souvenirs, one-of-a-kind items, and goods made by local artists. It is a great place to shop in the winter when you do not have to worry about the weather.
- If you want to relax inside, go to a local tasting room like Eastern Shore Brewing, Saint Michaels Winery, or Lyon Rum Distillery to enjoy seasonal drinks and stay warm.
Cozy Dining & Waterfront Views
- To warm up after the ChocolateFest crawl, go to one of St. Michaels’ restaurants or cafés for dinner or drinks. Many of them have comfortable indoor seats with views of the Miles River.
- Do not miss famous local restaurants or meals by the water that capture the seaside charm of the town.
Seasonal Charm & Events
Although not as crowded during the winter as during the summer it is a great place to visit during the weekend due to the small town beauty of St. Michaels and the friendly atmosphere. A lot of tourists like to take their time and walk along the ancient streets, eat food that is in season, and learn about the culture of the area.
Traveling from Annapolis: Expert Logistics
It is easy to plan your trip from Annapolis, Maryland to St. Michaels for ChocolateFest, and there are a lot of safe ways to get there and enjoy your stay.
By Car — Easy & Most Common
- It takes about 50 miles to drive from Annapolis to St. Michaels, which is the most common way to get there.
- The trip could take from an hour to an hour and a half, based on traffic and weather.
- Most people take Route 50 East across the Chesapeake Bay Bridge and then Route 33 south toward St. Michaels.
Public Transportation & Alternatives
- You can not take a bus or train directly from Annapolis to St. Michaels. To get to St. Michaels from the bus stops in Easton, which is about 10 miles away, you would need to take a cab or share a ride.
- If you really want to see some beautiful scenery, you could take a boat or tour from Annapolis along the Chesapeake Bay. Keep in mind that this is not a regular form of public transportation, so the timings may change.
Parking Tips in St. Michaels
- Once you get to town, you can park on the street or in a public lot near Historic St. Michaels. If you want to find a good place for an event like ChocolateFest, get there early.
- It is easy to walk from central parking lots to most attractions and event sites.
Comparison: Why 2026 is Different from 2025
The 2026 St. Michaels ChocolateFest has more activities and a new vibe than previous years, making it feel even more exciting for both returning tourists and people who have never been before.
More Chocolate Experiences
In 2026 local bakeries and restaurants are featuring many chocolate-themed beverages and meals throughout the town in limited edition. The pairing options of wine, beer, and spirits are more than in earlier years.
Broader Participating Venues
The Chocolate Crawl is the main event, but 2026 also offers wine and chocolate pairings and customized sample experiences at participating locations, delivering more structured activities than past editions.
Growing Festival Atmosphere
More companies and tourists are taking advantage of the festival’s activities, which is making it more well-known and drawing more people. This makes downtown St. Michaels busier than it was in the past, which brings in both locals and visitors from other towns.
FAQs — Everything You Need to Know
Is the event kid friendly?
Yes! ChocolateFest is a fun, family-friendly event where people of all ages can walk through Historic St. Michaels and try candy-themed treats from shops and restaurants. Casual and walkable, it is easy for families to enjoy together.
What happens if it rains or snows?
There is no rain at ChocolateFest’s big event, the Chocolate Crawl. That means the event continues even in rain, so guests should dress for the day’s prediction and wear comfortable shoes since participants will roam around town.
Can I buy tickets at the door?
You do not need to buy tickets ahead of time for the Chocolate Crawl; you just pay as you go at the participating businesses and get samples.
Depending on the place, special seated or curated tasting events like chocolate and wine pairings may need tickets or bookings ahead of time. You should make plans ahead of time if you want to do these things.
Are gluten free or vegan options available?
A lot of the participating bakeries and restaurants have choices for people with special diets, like chocolate treats that are gluten-free and sometimes vegan. Each seller has different stock, so it is best to check with each shop during the crawl.
What exactly happens at a chocolate festival?
At ChocolateFest, you’ll:
- Take a walk around town and try desserts and treats that are chocolate-themed.
- Go to bakeries, restaurants, cafes, and shops in your area that sell unique chocolate treats.
- You can choose to do unique tastings, such as pairing chocolate with wine or craft beer.
Today is a time to try new tastes of chocolate and celebrate all the different kinds of chocolate.
Does ChocolateFest have music?
Much of ChocolateFest is about chocolate tastings, but many downtown establishments and weekend activities provide live music or entertainment to enhance your stroll around Historic St. Michaels.