Get ready for a spooktacular evening of family fun in Downtown Watertown! Join us on Saturday, October 31, 2026, for our annual Pumpkin Palooza. Event Highlights: Trick-or-Treating | 2:00 – 4:00 PM Safe, fun, and perfect for kids of all ages. Stroll through Downtown and fill your bags with treats! Trunk or treaters from around Watertown are welcome to help us line the streets! If your business or organization is interested please contact info@dtnwtn.org for more information! 🍬 Costumes encouraged, smiles required! Bring your friends, your family, and your Halloween spirit to celebrate in the heart of our community. Where: Downtown Watertown When: Saturday, October 31, 2026 2-4pm Admission is free – everyone is welcome!

Kick off your Christmas shopping with Sparkle, Sip & Shop! Join Makepeace Jewelers for all things sparkle. Ladies, be sure to come ready to fill out your wish lists. Next, continue your way downtown and see what your favorite shops have for this year’s holiday season! Participating businesses downtown will be open until 7pm each Thursday night during the Holiday Season!

Enjoy the holiday season in the heart of downtown with an evening full of Christmas magic! Gather your family and friends downtown for our annual Tree Lighting Celebration, featuring festive music, holiday photo ops, sweet treats, and plenty of Christmas cheer. Watch as downtown comes to life with the lighting of our beautiful Christmas tree! Bring the kids, grab a warm drink, and enjoy the sights and sounds of the season while supporting your favorite downtown businesses. Whether you're starting your holiday shopping, making memories with family, or simply enjoying the magic of the season, there's something special about celebrating Christmas together downtown.

Kick off the holidays with a jolly good time at the 2nd Annual Downtown Santa Fun Run! Gather your family, friends, and neighbors for a festive 1-mile dash through the heart of downtown. Whether you’re a seasoned runner, a casual walker, or just here for the holiday fun, this event is for all ages and all speeds! Dress the part! Come all out in a full Santa get-up and join us for a morning filled with laughter, a whole lot of Santas, and plenty of holiday spirit! 🎄 EVENT DETAILS Start/Finish: Watertown Area Community Foundation Plaza Registration & Packet Pickup: 8:30 AM Run Starts: 9:00 AM Registration: $20 Early Bird & Student Discount After Nov 14 $25 Your registration includes: 🎽 Long-sleeve event T-shirt 🎅 Santa hat & beard (while supplies last!) 🏃 THE ROUTE We’ll follow a simple out-and-back course from the Watertown Area Community Foundation Plaza to Watertown Flowers and back. It’s a fun, family-friendly route perfect for runners and walkers of all ages! Children welcome with parental supervision. 🏆 PRIZES Best Dressed: Show us your holiday spirit for a chance to win! 🍺 Watertown Brewing Co. Challenge: The top three finishers age 21+ will be awarded pint prices based on their times for the ½-mile (6 minutes & under)! Grab your crew, throw on your Santa gear, and get ready to run, walk, laugh, and kick off the holiday season Downtown! 🎄🎅❤️ Registration is $20 sign up and let’s fill Downtown with SANTAS! https://square.link/u/FokgG8yd

Downtown Watertown is filled with the sounds of the holiday season! Enjoy an evening of festive music and performances throughout downtown as local musicians, choirs, and performers share their holiday favorites. Grab a friend, bring the family, and stroll downtown while taking in the sights and Sounds of the Season. ✨ Participating businesses downtown will be open until 7pm each Thursday night during the Holiday Season!

Satisfy your sweet tooth and explore downtown Watertown during the Cookie Crawl! Visit participating downtown businesses, collect delicious holiday cookies, and enjoy a festive afternoon of shopping, treats, and holiday cheer. Bring the family, grab your cookie bag, and stroll through downtown as you discover local businesses and sweet surprises along the way! This is limited to 200 bags! Don’t miss out! Register here: https://square.link/u/em9o24dv

Still have Christmas shopping to do? We’ve got you covered! Join us downtown for the Procrastinator Party, your last-minute chance to find those perfect gifts while supporting local businesses! Enjoy holiday specials, festive fun, and plenty of gift ideas as you check those final names off your Christmas list. No judgment, we’ve all been there! Participating businesses downtown will be open until 7pm each Thursday night during the Holiday Season!