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Middle Street Walk
Gloucester, MA
Historic street transformed with holiday cheer and diverse activities.
About
Step into a festive winter wonderland along Gloucester's historic Middle Street! This beloved annual walk transforms the charming street into a vibrant hub of holiday spirit. Discover local crafts, unique gifts, and delicious treats at various holiday fairs and cookie walks. Immerse yourself in the sounds of live music from brass bands to choirs, and explore historical buildings with guided tours. Don't miss the enchanting Gingerbread House Contest, a chance for horse-drawn hay rides, and the magical arrival of Santa Claus to light the Lobster Trap Tree.
Our Take
Family Friendly
Best For
Families, couples, and individuals looking for a festive holiday experience.
Vibe
Festive, community-oriented, historic, cheerful
Energy Level
Moderate
Budget
Varies (Free Activities, Some Paid Food/Crafts)
Photo Friendly
High
Weather Sensitivity
Moderate (some outdoor activities are weather-dependent)
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.
Location
Event Details
Duration
All day
Schedule
Day-long events include a Holiday Fair with local crafts and a cookie walk, thrift shop sales, self-guided stained glass tours, church fairs, and open house tours. Enjoy a Gingerbread House Contest, historical photos, and city hall tower tours. Experience live music from various bands, a children's holiday craft session, and behind-the-scenes tours of historic churches. Savor luncheons featuring fish stew, chili, and more. Take a horse-drawn hay ride along Middle Street with architectural tours. Explore historic 'Captain's Row' with museum walking tours. Enjoy bell choir concerts and performances by local dance and music groups. Visit the local synagogue for cider and sweets. Maritime Gloucester offers museum access, marine science activities, story time, and concerts. Santa Claus arrives to light the Lobster Trap Tree.
Featured Performers
- Reset Button Brass Band
- Cape Ann Big Band
- John Churchwell
- Jambalaya Horns
- Rockport Legion Band
- Miss Tina's School of Dance
- CAPE ANN ARTS ALIVE chorus
Organizer
middlestwalk
Practical Information
Pet Policy
No pets allowed
Food & Drink
Food trucks, cookie walk, luncheons, cider, hot cocoa, and baked goods available.
Tips & Advice
- Arrive early to enjoy the full day of activities, especially if you want to catch specific musical performances or tours, as some have limited capacity.
- Wear comfortable shoes as you'll be walking between various locations along Middle Street and exploring historic buildings.
- Check the schedule upon arrival for exact times of concerts, tours, and Santa's appearance to plan your day effectively.
- Bring cash for the various church fairs, craft sales, and food vendors, as not all may accept cards.
- Consider parking slightly further away and walking in, as the main Middle Street area can become quite busy.
Frequently Asked Questions
What kind of crafts can I expect to find?
You can expect a variety of local crafts, fine art, and seasonal goods from local makers and vendors at the various church fairs and holiday markets.
Are there activities specifically for children?
Yes, there are children's crafts, story time at Maritime Gloucester, and opportunities for photos with Santa Claus.
What are the food options available?
Food options include holiday cookie walks, luncheons at churches (like fish stew and chili), baked goods, hot cocoa, and food trucks.
Is the horse-drawn hay ride guaranteed?
The horse-drawn hay ride is offered weather permitting, so it's best to check conditions on the day of the event.
Can I tour the historic buildings?
Yes, many historic buildings like the Sargent House Museum and St. John's Episcopal Church offer self-guided or open house tours.