Holiday Shopping on the Chesapeake
Every December, the lovely coastal town of Annapolis, Maryland, becomes a Christmas attraction, and the Annapolis holiday Market is at the center of the entertainment. The Market is set against historic streets and the beauty of the Chesapeake Bay. It has a real mix of artisan goods, homemade gifts, seasonal cuisine, and a Christmas mood that makes it great for both residents and tourists.
The Market is back in 2025 with more sellers, family-friendly activities, and a new place to meet up. All of these things are meant to make you feel like you’re at a traditional Christmas market. The 2025 Annapolis Holiday Market is a must-see on your holiday schedule, whether you want to discover one-of-a-kind presents, taste holiday snacks, or soak up the festive atmosphere of downtown Annapolis.
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Dates, Location & Schedule for 2025
The Annapolis Holiday Market 2025 schedule will be open for two consecutive weekends, providing you plenty of time to come and enjoy the season.
- Week 1: Saturday, December 13 — 11:00 a.m. to 9:00 p.m.
- Week 2:
- Thursday, December 18 — 4:00 p.m. to 10:00 p.m.
- Friday, December 19 — 11:00 a.m. to 9:00 p.m.
- Saturday, December 20 — 11:00 a.m. to 9:00 p.m.
- Sunday, December 21 — 11:00 a.m. to 5:00 p.m.
Location
The Market has relocated from its usual spot at City Dock to the front lawn of St. John’s College this year. The entire location is 60 College Avenue, Annapolis, MD 21401, St. John’s College.
The move to the college lawn makes room for the event to develop and gives guests a large, joyous space.
Why the new place? City Dock, where the Christmas market used to be, is being renovated. Transferring the Market means it can keep operating without interruption and give the college grounds a new festive feel.
Tips for First-Time Visitors
- Plan by day and time: If you’re planning on attending on more than one day, you have more flexibility to choose when the events take place; nonetheless, if you’re looking for a more tranquil experience, try going on a Thursday night or a Sunday afternoon.
- Arrive at the correct time: Expect the most people on Saturday, December 13, or the weekend days of December 20 and 21, between 11:00 a.m. and 4:00 p.m. If you want to make it simpler to look around, try going on Thursday after 4 p.m. or Sunday afternoon.
- Combined with other downtown holiday events: The Market is part of a bigger Christmas celebration in Annapolis, with city-wide festive lights, decorations, and seasonal charm. An entire day of shopping, eating, and touring may make it seem even more memorable.
- Free entry: You don’t need tickets to get into the Market, so you can just show up.
Vendors and Shopping: What to Buy at the Annapolis Holiday Market
The Annapolis Holiday Market vendors has more than 100 artisan and specialty food vendors, making it one of the greatest venues in Maryland to conduct thoughtful, handmade holiday shopping. These sorts of merchants and things you can buy:
- Handmade crafts and art: Many sellers provide one-of-a-kind, handmade items, including ceramics, glass art, home décor, original art prints, and bespoke decorations.
- Jewelry and accessories: handmade jewelry, wearable art, and other handmade items are prevalent and make great gifts for friends and family.
- Gifts and decorations for the holidays: seasonal ornaments, festive decorations, wreaths, candles, and other holiday-ready goods that fit the Christmas market feel.
- Specialty foods and treats: As part of the Market’s appeal, sellers also sell small-batch holiday delicacies, including baked goods, seasonal delights, artisan meals, and gourmet products. These are great gifts for friends or family who love food.
- Local & regional gifts—many of the craftsmen and sellers are from Maryland and the Chesapeake region, so you may buy things that show off local skill and flavor.
Why Does this Market Stand Out?
The Market wants to keep it homemade and artisan-focused on purpose: only sellers who manufacture their own things are allowed.
There are more than 100 sellers, so you’ll have a wide range of options, from cheap little presents to more expensive, unique gifts. That means you can find presents for kids, parents, friends, colleagues, and even yourself all in one spot.
What’s New or Especially Worth Checking Out in 2025
- The Annapolis Holiday Market 2025 vendors still has a mix of crafts, art, home décor, jewelry, and gourmet foods, making it a great place to purchase high-quality homemade presents throughout the holidays.
- The Market has moved to the front lawn of St. John’s College (60 College Ave, Annapolis, MD), which makes the layout more open and gives consumers a casual, stroll-through experience.
- It’s simple to combine shopping with holiday delights when there are specialist food booths next to art and gift shops. This is great if you want both presents and culinary souvenirs.
More Than Shopping: Food, Drink, and Festive Activities
The Annapolis Market is more than just a place to look at vendor booths. It’s also a wonderful holiday celebration with food, beverages, live entertainment, and activities for the whole family.
Food & Drink Delights
- The Market has a lot of seasonal drinks and snacks to choose from. Expect warm drinks like hot chocolate, hot apple cider, and spiced wine, as well as holiday treats like strudels, cookies, and other sweet treats.
- If you’re in the mood for something savory, several specialized food sellers provide substantial dishes, from warm soups and comfort meals to regional specialties, that are excellent for walking through the cold streets in the winter.
- The Holiday Market is a great place to get both presents and food for friends and family since it has both.
Festive Activities & Live Entertainment
- There is a lot of activity going on in the Market every day. You can anticipate live music and stage performances from local bands and young vocal groups, which gives the Market a festive, holiday feel.
- Past editions, for example, included a “Jolly Express” cruise, holiday-themed concerts, and a wide range of acts that were appropriate for people of all ages.
Family‑Friendly & Holiday Traditions
- Families are welcome at the Holiday Market. There are regular meet-Santa times where kids (and adults!) may take complimentary pictures, which is a great, classic holiday touch.
- In addition to the Market itself, the downtown area of Annapolis, Maryland, sometimes has other Christmas activities at the same time, such as tree lightings, holiday boat parades, walking tours, and streets adorned for the season. This makes it easy to transform your visit into a complete holiday adventure.
Insider Tip: The best way to enjoy the Market is to think of it as a little vacation. Get a hot cider or spiced wine, look at handmade products, listen to live music, and walk about downtown Annapolis to see the decorations and get into the Christmas spirit. The Annapolis Holiday Markets has something for everyone, whether you’re coming to buy presents, eat, or get into the holiday mood. Over 100 craftsmen and food sellers are still there, and the entrance is free.
Navigating the Annapolis Holiday Market
Where & How to Get There
- You may find the 2025 holiday market annapolis on the front lawn of St. John’s College at 60 College Avenue, Annapolis, MD 21401.
- The Calvert Street Parking Garage (19 St. John’s Street) is the best place to park. It has free parking after 6 p.m. on weekdays and all day on weekends.
- The Whitmore Parking Garage (25 Clay Street) and the Gotts Court Parking Garage (25 Northwest Street) are also close to the Market; however, some may charge depending on the time of day.
- If you’re using public transportation, the Annapolis Transit bus system may take you to downtown Annapolis and put you off close enough to St. John’s College to walk there.
- The best place to drop off a group or tour bus is at the entrance on College Avenue and St. John’s Street.
- Tip: Street parking in the city center usually has strict time limitations, so the parking garages are the ideal place to park for a stress-free stay.
Ideal Times & Crowd Navigation
You may choose when to go to the Market in 2025 since it happens over two weekends:
Week 1: Saturday, December 13, from 11 a.m. to 9 p.m.
Week 2: Thursday, December 18 (4 p.m. to 10 p.m.), Friday, December 19 (11 a.m. to 9 p.m.), Saturday, December 20 (11 a.m. to 9 p.m.), and Sunday, December 21 (11 a.m. to 5 p.m.)
- If you want a more peaceful visit, think about visiting Thursday night (after 4 p.m.), when there will be fewer people, just as the Market begins.
- Sunday afternoon, particularly before the store closes at 5 p.m., is also a calmer time as people start to thin out.
- If you attend on Friday or Saturday between noon and 4 p.m., when the Market is busiest, anticipate more crowds. This is great if you like the busy market atmosphere.
- Also, as the Market is held on a lawn at St. John’s College instead of on narrow sidewalks or busy city-dock streets, it will be simpler for you to wander between vendor booths and enjoy the more open space.
Entertainment, Events & How to Enjoy Them
- The Market isn’t only for buying. There are other fun events going on to make your visit more special.
- There will be live events, such as bands and dancing performers, throughout the festival days for visitors to enjoy.
- Families may take pictures with Santa and get a chance to “meet Santa.”
- You may get the whole downtown Christmas experience by going to the Market and then going to other holiday activities nearby, such as holiday lights, decorated shops, seasonal walking tours, and shopping and eating downtown.
Suggested flow: Arrive in the middle of the day (when crowds are less), park at the Calvert Street Garage, enjoy walking among the vendors, have a warm drink or snack, see a live performance or Santa, and then go to downtown Annapolis for supper or a walk under the Christmas lights.
Essential Logistics: Parking & Accessibility
Parking Options Near the Market
- The Market for 2025 is on the front lawn of St. John’s College (60 College Ave, Annapolis, MD), which is just a short walk from the historic streets and stores of downtown Annapolis.
- The Calvert Street Parking Garage (19 St. John’s Street) is the best place to park since it’s just a block from the market entrance. Calvert Street Garage has free parking on all weekends and on weekday nights after 6 p.m. in 2025. This is great for trips on weekends or in the evening.
- You may also walk to the Whitmore Parking Garage (25 Clay Street) and the Gotts Court Parking Garage (25 Northwest Street).
- There is parking on the street between St. John’s Street and King George Street; however, keep in mind that many of these places have strict time limitations.
- The city has a holiday parking scheme from Thanksgiving to New Year’s Day. It lets people park for free for two hours in metered and kiosk spots (via the ParkMobile app) in several downtown locations and some garages.
Tip: The quickest method to avoid time limitations or getting a citation is generally to park in the Calvert Street Garage or a neighboring paid or reduced garage. This is particularly true if you want to shop, dine, or walk about downtown for a few hours.
Public Transit, Bike & Shuttle Options
- Annapolis Transit is the public bus service in Annapolis and its surrounds. If you don’t want to park at all, this might be a good choice.
- If you’re driving in and want to avoid parking problems downtown, certain garages outside the main city zone provide shuttle or trolley services (such as the “Purple” or “Ten-Minute” trolleys) to take you downtown. This is a handy Park-and-Ride alternative.
- You may also ride your bike downtown since there are bike racks near parking garages, historic landmarks, and commercial areas. This makes it simple to cycle there and lock up your bike if the weather is favorable.
Accessibility & Special Parking
- All of the parking garages in downtown, such as Calvert, Whitmore, Gotts, and others, include accessible parking spots for cars with a disability sticker or license plate.
- Some commercial and important downtown locations have defined accessible parking places on the street. If you have a disability placard, some street parking time limitations may be longer (for example, “double the time posted” in some sites). Be sure to check the signs before you park.
- The event will take place on the green lawn of St. John’s College. It should be simple to get about on foot, but if you have trouble walking, parking in a garage with accessible parking and using shorter walks (like from Calvert Street Garage) is probably the best choice.
Other Considerations (Pets, Group Visits, Event‑Day Flow)
- For group trips or tour buses, the organizers say that big groups and buses are welcome. There is a suggested drop-off area near the market entrance that might make it easier to get there if you have a lot of people or big products.
- It’s a good idea to plan, particularly if you’re going during busy times (weekends, nights), since parking in the downtown area is typically restricted and rigorously regulated. Consider using parking garages or public transportation to make things easier.
Conclusion: Get Your Holiday Shopping Done Early
Searching for holiday bazaar 2025 near me? The West Annapolis Holiday Market offers a complete holiday shopping experience, with early access in 2025. Over 100 craftsmen and specialized food vendors provide unique, handmade goods, including jewelry, ceramics, sweets, and décor, not seen in normal shops.
Admission is free, and the Market is held over two weekends (December 13 and 18-21) in St. John’s College’s beautiful front lawn, making it a handy and stress-free setting for early Christmas shopping.
The Market offers presents, seasonal décor, warm beverages and food, and time with friends and family as part of a festive excursion around downtown Annapolis, Maryland.
Please mark your calendar today to attend the Annapolis Holiday Market, bring friends, and make it an annual tradition. Share your treasures and joyful moments on social media to spread joy!