There is a distinct rhythm to Memorial Day weekend in our corner of Fairfield County. The stone walls are lined with American flags, the main streets fill with neighbors, and the sound of marching bands echoes through the spring air. It is a weekend where we pause to honor those who made the ultimate sacrifice, while collectively welcoming the warm days ahead.
To help you plan your weekend, we have mapped out the key events, timetables, and insider strategy for each town.
1. Weston: The Saturday Kickoff
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The Main Event: The 32nd Annual Weston Memorial Day Weekend 5K & Kids Fun Run
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When: Saturday, May 23, starting at 7:45 AM for the kids and 8:30 AM for the 5K
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Where: Weston High School Weston kicks off the holiday weekend early with one of the most popular community fundraisers of the year. The USATF-certified 5K route takes runners through a scenic, tree-lined course in the heart of town. Even if you are not running, the energy at the high school track is fantastic, featuring a Kids Fun Zone with a massive inflatable obstacle course. It is the perfect place to grab a morning coffee and catch up with neighbors.
2. Westport: 250 Years of Honor and Service
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The Main Event: The Westport Memorial Day Parade and Services
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When: Monday, May 25, starting at 9:00 AM
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Where: Riverside Avenue to Parker Harding Plaza The 2026 parade theme is 250 Years of Honor & Service, and the town is planning an exceptional lineup.
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The Route: The parade begins at Saugatuck Elementary School, heads north on Riverside Avenue, turns east onto Post Road East, moves down Myrtle Avenue and Main Street, and wraps up at Parker Harding Plaza.
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Insider Tip: Immediately following the march, step over to Veterans Green on Myrtle Avenue for the commemorative memorial services. If you have guests in town, wrap up the morning by heading down to VFW Post 399 at 465 Riverside Avenue around noon, where they host their traditional free buffet luncheon for veterans and the community.
3. Wilton: The Historic Flyover
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The Main Event: The Wilton Memorial Day Parade and Cemetery Ceremony
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When: Monday, May 25, starting at 10:00 AM
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Where: River Road through the Town Center to Hillside Cemetery Wilton’s parade is a stunning, classic New England display.
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The Highlight: Keep your eyes on the sky. The 2026 parade will feature a spectacular military flyover by a C-130 aircraft traveling the length of the parade route.
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Road Closure Alert: Roads along the route, including parts of Ridgefield Road and Horseshoe Road, close at 9:30 AM. Plan your parking early in the outer town center lots. The parade concludes with the moving traditional ceremony at Hillside Cemetery, and all roads fully reopen by 12:30 PM.
The Marion Filley Team Long Weekend Strategy
If you are trying to maximize the weekend, the perfect itinerary looks like this: spend Saturday morning cheering on the runners in Weston, utilize Sunday for a quiet hike at Devil's Den or a beach walk at Compo, and pick your favorite parade route for Monday morning.
What makes the 3 Ws so special during the holidays is the sheer scale of participation. These are towns where people do not just watch from the sidelines; they march, they volunteer, and they show up to remember together!
