Middle Street Walk
2026 dates not announced yet. Details are from 2025.
Step back in time at the Middle Street Walk, a cherished holiday tradition. Explore historic churches and buildings, browse local crafts, and enjoy festive food. Highlights include a Gingerbread House Contest, live music, horse-drawn hay rides, and a unique Lobster Trap Tree lighting ceremony. It's a day of community, history, and holiday cheer.
All ages $
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Plan Your Visit
Last listed
Neighborhood
Middle Street Historic District
Featured Performers
- Reset Button Brass Band
- Cape Ann Big Band
- John Churchwell
- Rockport Legion Band
- Jambalaya Horns
- Miss Tina's School of Dance students
- CAPE ANN ARTS ALIVE chorus
- Gloucester Student Band
Food & Drink
Food trucks, holiday cookies, fish stew, clam chowder, hot dogs, chili, egg salad sandwiches, cider, sweets, hot cocoa available.
Location
Tips & Advice
- Arrive early to secure parking, as many activities are concentrated along Middle Street and popular venues fill up quickly.
- Check the specific times for scheduled events like concerts and tours, as they are staggered throughout the day.
- Wear comfortable shoes as you'll be walking between various historic locations and participating in tours.
- Bring cash for food purchases and any small craft items, as not all vendors may accept cards.
- Dress in layers and check the weather forecast, as some activities like the hay ride are weather-dependent.
Special Events & Promotions
- Gingerbread Creation Contest
- Horse Drawn Hay Ride
- Lobster Trap Tree Lighting
- Santa photos
Links & Contact
Christmas Events Near Me is an independent guide, not the organizer of this event. For tickets, entries, vendor spots or questions, contact the organizer directly through their website.
Frequently Asked Questions
What is the Middle Street Walk?
The Middle Street Walk is an annual holiday event in Gloucester that transforms historic streets and buildings into festive attractions with various activities, crafts, food, and music.
Are there activities for children?
Yes, there are several children's activities, including a holiday craft session with the Sawyer Free Library and a Gingerbread Creation Contest.
What kind of food is available?
A variety of food options are available, including holiday cookies, fish stew, clam chowder, hot dogs, chili, and treats from food trucks like The Cravery and The Lobster Roller.
Is there live entertainment?
Yes, the event features live music throughout the day from various bands and performers, including the Reset Button Brass Band and the Cape Ann Big Band.
What is the Lobster Trap Tree lighting?
The Lobster Trap Tree lighting is a unique Gloucester tradition that marks the culmination of the day's festivities, often with Santa's arrival.
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Always check the official website for the most current information.
We've done our best to keep details up-to-date, but event schedules, prices, and policies can change. For the latest updates, please visit the official website or contact the organizers directly. Christmas Events Near Me is an independent guide and isn't affiliated with the events we list.