Every year, Brimfield turns into a picker’s paradise—but did you know it can also be a kid-friendly adventure with the right game plan? As a local parent and your Macaroni KID guide, I’ve learned how to navigate the mile-long stretch of vintage booths with little ones in tow. This guide is full of family-tested tips, fun finds, and the “we always stop here” spots my kids look forward to every show.
🗺️ How I Break Up the Brimfield Strip (Parent Map Style)
Brimfield stretches along Route 20 and is made up of multiple fields with their own entrances. It can feel overwhelming, so I break it up into 3 manageable zones:
1️⃣ East End
Start near the Brimfield Library and work your way into the quieter fields or vice versa.
Good for:
- Vintage Clothing — These tents can get crowded with a stroller, and honestly, I rarely find children’s clothing that isn’t baby sizes. (If anyone finds a kids' clothes booth, let me know!) But worth a stroll if you have a fashionista or two in tow!
- Metal Art Displays — Across the street, you’ll find large metal outdoor sculptures. This week’s favorite? An Extra-large
flamingosLobster this week! There’s always something whimsical that the kids enjoy. - Brimfield Winery — On the left side, perfect for a late afternoon wine slushie 🍷, and it has a fenced garden where the kids can stretch their legs and run.
- Kitchen & Decor Booths — As you head west, booths turn from clothing to kitchenware and curated vintage decor. My favorite? The booth with windchimes and posters—there’s something for everyone!
- Toy Booth with $3 Monster Trucks — Always a hit with my little ones.
Kid Tip: There’s plenty of space between booths. If one feels crowded or not stroller-friendly, no stress—there’s more around the corner. Having a few break spots where the kids can run is key!
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2️⃣ Midway Magic (Food + Break Time)
This is your reset zone! Around the central food court areas is where we pause, refuel, and regroup.
Favorites:
- Hertan’s Maple Tent – Cider slushies, maple cotton candy, and more snacks. My kids count down the days for this!
- Metal Toy Truck Booth in Hertan's – Super sturdy trucks, and the vendor even sets some out to play with—huge win!
- Stone Garden – Just across the street, this beautiful area brings a little magic to the market. My kids love wandering through it.
- New England Motel Food Court – A lineup of food trucks with something for everyone. Try the fresh-squeezed lemonade, grilled cheese from the Say Cheese truck!
Bonus: Many booths here have fun visuals—globes, vintage signs, marbles, buttons—and lots of toys the kids can explore while you shop
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3️⃣ West Fields (Treasure Hunt Time!)
The final stretch is home to eclectic and creative vendors, perfect for curious kids.
What My Kids Love:
- Weird taxidermy and quirky old objects
- Old keys and trinket bowls where they can pick their own treasure
- Brimfield Barn – A must-see with fascinating displays
- Fred’s Booth – Don’t miss my friend Fred! (You’ll spot us in the photo gallery.) He’s handing out stickers and red clown noses—a total hit with kids!
- Garden booths – Think birdhouses, statues, and fun outdoor decor
Parent Tip: This is a great zone to split up—one grown-up shops while the other explores nearby with the kids.
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What My Kids Look Forward to Every Year
- The Vermont Maple Tent — Slushies + maple cotton candy = instant joy
- Finding a “treasure” under $5 — Vintage matchbox cars, dolls, and Barbies are the top picks
- People-watching & Dogs — Friendly pups on leashes make it feel like a local block party
- Shade breaks — We pack snacks + a small blanket or chair to chill while I browse
🧺 Parent Packing List
- Water bottles
- Umbrellas & rainboots (this show's weather is wet!)
- Sunscreen + hats
- Foldable stroller or wagon
- Cash and card (some vendors only take one)
- Wet wipes & hand sanitizer
- A tote or backpack for the kids’ treasures
- A meeting spot in case you get separated (we choose a landmark!)
🛍️ Insider Tip: Make it a Game
We play Brimfield Bingo or “Spot the Weirdest Thing” to keep the kids engaged while walking through rows of booths.
📍 When to Go
- Early mornings = cooler + less crowded
- Weekdays are calmer than weekends
- Avoid high noon if your kids are heat-sensitive or prone to crankiness
👣 Final Tip: You Don’t Have to Do It All
Brimfield is BIG. Your kids will still have a blast even if you only make it through a few fields. We almost always go every week it’s open, and we’ve never managed to make it through the whole show in one day.
Pick a direction, pace yourself, and soak it all in. And if you’re treasure hunting something specific, good luck and happy digging!
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