Boston in the fall is magic — crisp air, golden leaves, and a calendar packed with events that celebrate the city’s history, creativity, and flavor. Whether you’re a foliage fanatic or just looking for a new way to spend a Saturday, these upcoming pop-ups and happenings are worth adding to your fall bucket list.
Here are 10 must-see events lighting up Boston this autumn:
🍁 1. Seaport Autumn Market Nights
Location: Seaport Common
Date: Every Thursday in October
An after-hours twist on the traditional fall fair. Expect locally made candles, warm cider cocktails, indie music, and photo-friendly harvest decor under the skyline. Think farmers market meets night out.
🧡 2. Back Bay Pumpkin Lane
Location: Newbury Street
Date: October 5–6
Boutique storefronts will be decked in pumpkins and gourds for this festive stroll. Look out for seasonal menus, free samples, and sidewalk pop-ups from Boston’s best small brands.
🍺 3. Fenway Fall Fest & Beer Garden
Location: Lansdowne Street
Date: September 27–29
Local breweries + live folk rock = the perfect combo. This 3-day block party features craft beer tastings, fire pits, and rotating food trucks, all in the shadow of Fenway Park.
🎃 4. The Great Pumpkin Glow at Boston Common
Location: Boston Common
Date: October 19
Hundreds of artist-carved jack-o’-lanterns will light up the Common for one night only. Free entry, live carving demos, and glowing treats for kids.
🖼️ 5. South End Open Studios
Location: Throughout the South End
Date: September 14–15
Meet Boston’s most creative minds in this neighborhood-wide open studio event. From painters to ceramicists, it’s the perfect place to shop local art and see how it’s made.
🧪 6. MIT’s Great Glass Pumpkin Patch
Location: Kresge Lawn, MIT
Date: October 12
Every pumpkin here is handmade from blown glass by MIT’s Glass Lab. A favorite for collectors and families — and a rare peek into one of the school’s coolest crafts.
☕ 7. Boston Public Market’s Cider & Donut Days
Location: Boston Public Market
Date: Fridays & Saturdays, all season
Fresh apple cider and cider donuts, seasonal produce, and live music indoors. Warm up your hands and fill your tote.
🕯️ 8. Witchy Pop-Up at Bow Market
Location: Somerville (Bow Market)
Date: October 20–31
From tarot readings to vintage spellbooks, this Halloween pop-up celebrates all things spooky and magical. Perfect for some seasonal shopping and a haunted espresso martini.
🚲 9. Tour de Foliage: Bike Boston’s Scenic Loop
Location: Charles River Path → Emerald Necklace
Date: Self-guided, mid-October peak
Grab a Bluebike or your own wheels and explore the Charles River’s vibrant colors, connecting to the Emerald Necklace. This unofficial “tour” peaks in mid-October, and some local shops offer guided rides.
🎭 10. Shakespeare in the Fall: Macbeth
Location: Boston Common (Parkman Bandstand)
Date: September 21–24
A moody, dramatic outdoor performance of Macbeth by Boston Common Theatre Co. Arrive early, bring a blanket, and let the leaves fall around you.
🍂 Bonus Tip:
Check out @bostonweekly on Instagram — we’ll be spotlighting each of these events with live coverage, photo roundups, and last-minute pop-up announcements all season long.
Which event are you most excited for? Let us know in the comments or tag us in your fall adventures with #BostonInTheFall.