Rockland Holiday Stroll 2026

November 15, 2022 admin

ROCKLAND HOLIDAY STROLL IS BACK for 2026

Make plans for a festive afternoon in Rockland! The Rockland Holiday Stroll takes over Union Street on Saturday, November 28th, from 3–6 PM, with plenty of holiday fun for the whole family!

This is a great Christmas holiday event for the entire family over the Thanksgiving weekend

Each year on the Saturday after Thanksgiving, Rockland community members and businesses come together in the center of town to kickstart the holiday season and spread some holiday cheer! From Rockland’s very own North Pole at the Magoun-Biggins home featuring Santa and Mrs. Claus themselves to magical hayrides through the streets of town and Joe’s Crazy Critters in Town Hall – there is always plenty of family friendly holiday fun at the Stroll.

Join us as the town of Rockland comes together on Union Street to kickstart the holiday season this year!
We are excited to see everyone at the Stroll this year – we’ve heard from the Claus’ 🎅🏻🤶🏻themselves that they can’t wait to come back to Rockland to join us in our celebration and see all of the good people of Rockland once again this year!

Join our Shopping Deals Group including Local businesses

✨ Here’s what you can look forward to:

🎅 Visit the North Pole with Santa & Mrs. Claus
🎪 Watch the amazing stilt walker from Aerialicious Entertainment in the MountainOne area!
🐍 Meet fascinating reptiles with Joe’s Crazzy Critters at the Rockland Fire Station
🥋 Stop by South Shore Tae Kwon Do for an open house, demonstrations and activities
🎶 Enjoy live street performances
🎨 FREE family activities
🍔 Delicious food and a Beer Garden
🎄 And so much more!

Bring the family, grab your friends and kick off the holiday season with an afternoon of festive fun!

📅 Saturday, November 28, 2026
⏰ 3–6 PM
📍 Union Street, Rockland, MA