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Weekend Event Guide (Sept. 20-22)

By Jenna Amyot September 18, 2024

It looks like this weekend will bring some fall-weather feeling days and I'm here for it.  My hydrangeas are burnt to a crisp and so is about everything else in my yard, so I'm ok with some rain in the forecast, and I'm sure you are too! There's so much going on this weekend and I know fall sports and activities are already in full swing, but I hope you're able to check them out as a way to reconnect with your family and unwind from all of the craziness that back to school brings upon us. As always, my event calendar is packed, so be sure to check that out. Have a great weekend!

Winchester: Spirit Weekend, Friday-Sunday 

Spirit Weekend is fun-filled event that takes over the streets of downtown Winchester, includes a Friday Night Lights-esque football game, a performance by the infamous Pogo Fred (it's exactly what it sounds like), a beer garden, a road race in honor of local fallen hero Glen Doherty and a bottomless brunch at A Tavola. It spans Friday, Saturday and Sunday, so there's plenty of time to check it out with your families!

Arlington: Town Day (Saturday)

Town Day in Arlington is an annual tradition dating back to 1976! And, it gets bigger and better every year. This year, you can enjoy live music and peruse more than 200 booths from local businesses and artisans, which is a great away to appreciate and support those who lift up our communities. And, one plus side of the sun setting earlier these days is that fireworks start at a reasonable time for those of us with young kids - with fireworks starting over Spy Pond at 7:30. Roads will be closed on Mass Ave. between Pleasant St. and Jason/Mill St. 9:15 a.m. - 6:15 a.m. 

Arlington: Taste of West Medford Square (Saturday)

Want to sample West Medford establishments all at once? Then head on over to the Taste of West Medford Square on Saturday. Admission is free, but food and drinks will be available for purchase at the participating restaurants!

Medford: Mystic River Celebration (Saturday)

This is another great, family-friendly event on deck for the weekend, this one at Medford's Condon Shell. There will be live music, poetry, food and activities for the kids. And who knows, maybe the fall foliage will be showing off for us (reminder: here's when fall foliage will peak in our communities)

Woburn: Conquer Chiari Walk Across America (Saturday) 

This one is near and dear to my heart - the Conquer Chiari Walk Across America takes place in September and walks happen all across the country - with the Massachusetts walk taking place at Library Park in Woburn. This walk is the single biggest fundraiser for Chiari Malformation, a neurological disorder that needs more research. 

Somerville: What the Fluff Fest (Saturday)

Fluff was a huge part of my childhood and it kills me that I've never been able to attend the What the Fluff Fest (mostly because I didn't hear about it until after it happened), so if you'd like to revisit the nostalgia of Fluffernutter sandwiches (and more), then this is your PSA that the What the Fluff Fest is this Saturday!

Woburn: Sunday Shops at Woburn Village (Sunday)

Woburn Village is such a great new-ish spot that is always adding great new businesses. But, I especially love how they have a green space for events (like movie night) or Sunday Shops. It's a great opportunity for a shop and stroll.