WINdependent Weekend is our favorite way to kick off the holidays in Old Town — three days dedicated to celebrating and supporting the small businesses that make our downtown feel like a real community.
Throughout the weekend, shops and restaurants will have specials, treats, and festive surprises. It’s the perfect chance to knock out some holiday shopping, explore new spots, and enjoy everything that makes Old Town shine this time of year.
What’s Happening
Plaid Friday – Nov 28
Start the weekend off with something fun. We’ll be out on the bricks handing out Old Town–themed merch, little prizes, and a Retail Bingo sheet. Visit shops, fill out your card, and you’ll be entered into a raffle with some great local giveaways. Wear your plaid, support your neighbors, and enjoy a relaxed, hometown version of Black Friday.
Small Business Saturday – Nov 29
Our biggest shopping day of the year. Local businesses will be offering specials, pop-ups, and plenty of ways to show love to the people who keep our downtown running year-round.
Sunday Stroll – Nov 30
A laid-back way to wrap up the weekend. Grab a warm drink, wander the mall, and take your time enjoying the holiday atmosphere.
Old Town’s independent businesses are the heartbeat of our pedestrian mall. Shopping small this weekend directly supports the people, families, and stories that make Winchester special.
Merchant specials and the full bingo lineup will be posted soon — stay tuned!
You may also like the following events from Friends of Old Town:
