Head of the Charles Regatta along the Charles River Basin
Watch thousands of world-class rowers slice through the water framed by blazing autumn foliage, best viewed from the Weeks Footbridge or Eliot Bridge.
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For familiesThings to do in Boston with kids this weekend (Oct 16–18)
This weekend in Boston: Fri, Oct 16 – Sun, Oct 18, 2026 · 7 dated events
Family activities in Boston, MA right now: kid-friendly events the whole family will like, restaurants that can handle a toddler, and weekend ideas that work around nap windows.
13 hand-picked things to do in Boston, MA right now · 7 with confirmed dates
Photo: jacob Licht / Unsplash
How we pick family-friendly spots
- Stroller- and toddler-friendly venues with room to move
- Weekend and daytime timing that works around nap windows
- Kids-eat-here restaurants over date-night-only rooms
🚣 This Weekend in Boston, MA · Oct 16–18
Autumn traditions and riverside racing
Harvard Crimson vs. Holy Cross Crusaders at Harvard Stadium
Crisp autumn college football in the nation's oldest concrete stadium, complete with tailgating and classic New England rivalry energy.
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The Pierre Hurel Trio at Regattabar
Sip craft bourbon and unwind to lyric post-bop piano jazz inside Harvard Square's premier listening room after walking the river.
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Plan a family trip to Boston, MA
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🍁 Happening Today
Events and things to do tonight
Wicked (Touring) at Citizens Opera House
Escape the crisp mid-October breeze for an afternoon inside the gold-leaf splendor of the Opera House as the Broadway smash takes the stage.
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Sylvan Esso at Citizens House of Blues
Amelia Meath and Nick Sanborn bring their synth-pop rhythms and hypnotic stage energy to Lansdowne Street for a sharp Saturday night set.
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Beck: Ride Lonesome Tour at MGM Music Hall
An intimate evening with the genre-bending icon touring fresh acoustic and orchestral arrangements right next door to Fenway Park.
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✨ New & Notable
Seasonal pop-ups and timely happenings
Seasonal Autumn Afternoon Tea at The Street Bar
Revived for the chilly season, featuring warm buttermilk scones, butternut squash carpaccio tea sandwiches, and spiced pumpkin pastries by the hearth.
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Peak Canopy Walks at Harvard's Arnold Arboretum
Peter's Hill and the Hunnewell Building grounds reach peak bronze and amber this week—bring a thermos of hot cider for the skyline vista.
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🚗 Quick Escape
Road-trip getaways under 3 hours away
Salem Historic Harbor & Haunted Happenings
Hop the commuter rail or take the 45-minute drive up Route 1A for 17th-century maritime history, spiced cider donuts at Derby Wharf, and Salem's peak October street atmosphere.
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Mount Monadnock & Peterborough Countryside
Head two hours northwest into southern New Hampshire to hike the white arrow trail for 360-degree foliage views, followed by clam chowder and warm apple crisp in Peterborough.
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🍷 Eat & Drink
Warm dining rooms and autumn flavors
Wood-Fired Autumn Tasting at Fallow Kin
Rooted in the former Craigie on Main space, this farm-to-table haven turns out roasted squash with spiced cider reductions and handmade agnolotti.
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Vintage Champagne & Small Plates at 89 Charles
Tucked among the gas lanterns of Charles Street, order dry cider cocktails and savory duck fat potatoes in an intimate, brick-lined den.
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Northern Italian Brunch at Contessa
Perched glass-enclosed atop The Newbury, enjoy warm torta baciata and spicy lobster rigatoni while overlooking the gold-tinged Public Garden.
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Ready-made Boston, MA itineraries
Ready-made plans for Boston, MA, written out in full and built from real local spots — start from one instead of a blank page.
Frequently asked
What are the best things to do in Boston, MA with kids?
Family-friendly highlights right now include Wicked (Touring) at Citizens Opera House, Sylvan Esso at Citizens House of Blues, and Beck: Ride Lonesome Tour at MGM Music Hall. WonderKit refreshes this Boston, MA guide daily so the picks stay current.
Where can families eat in Boston, MA?
The "Eat & Drink" section above lists restaurants that work for families in Boston, MA, including spots that handle toddlers and offer kid-friendly menus.
What's happening in Boston, MA this weekend with kids?
Check the "This Weekend in Boston, MA" section above for current family-friendly events and weekend activities in Boston, MA. Updated daily.
Plan a family trip to Boston, MA
Tell us who's going and WonderKit drafts three Boston, MA trip ideas in about a minute — free, and you see them before creating an account.