# Things to Do in Boston with Kids This Weekend \(Oct 16–18\)

Things to do in Boston with kids this weekend, Oct 16–18: 7 dated events, family activities, kid-friendly restaurants and weekend ideas. Updated Oct 17.

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This weekend in Boston: Fri, Oct 16 – Sun, Oct 18, 2026 · 7 dated events

Updated: Oct 17, 2026

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.

## 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.
- Venue: Citizens Opera House
- Location: Downtown Crossing, Boston
- Date: 2026-10-17 2:00 PM
- Cost: $$$
- Best for: Everyone
- Link: https://www.axs.com/events/538743/wicked-tickets

### 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.
- Venue: Citizens House of Blues Boston
- Location: Fenway-Kenmore, Boston
- Date: 2026-10-17 7:00 PM
- Cost: $$
- Best for: Adults
- Link: https://www.livenation.com/event/G5vjZbd1E4-Xl/sylvan-esso

### 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.
- Venue: MGM Music Hall at Fenway
- Location: Fenway, Boston
- Date: 2026-10-17 7:30 PM
- Cost: $$$
- Best for: Adults
- Link: https://www.livenation.com/event/G5vjZbdJ7n4t2/beck-ride-lonesome-tour

## This Weekend in Boston, MA

Autumn traditions and riverside racing

### 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.
- Venue: Charles River
- Location: Cambridge & Allston, Boston
- Date: 2026-10-17 7:45 AM
- Cost: $
- Best for: Everyone
- Link: https://hocr.org/the-regatta/schedule/

### 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.
- Venue: Harvard Stadium
- Location: Allston, Boston
- Date: 2026-10-17 1:00 PM
- Cost: $$
- Best for: Everyone
- Link: https://fbschedules.com/harvard-adds-holy-cross-to-2026-football-schedule/

### 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.
- Venue: Regattabar
- Location: Harvard Square, Cambridge
- Date: 2026-10-17 7:00 PM
- Cost: $$
- Best for: Adults
- Link: https://www.ticketweb.com/event/the-pierre-hurel-trio-regattabar-tickets/14925013

## 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.
- Location: Central Square, Cambridge
- Cost: $$$
- Best for: Food Lovers
- Link: https://www.google.com/search?q=Wood-Fired%20Autumn%20Tasting%20at%20Fallow%20Kin%20Central%20Square%2C%20Cambridge

### 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.
- Location: Beacon Hill, Boston
- Cost: $$
- Best for: Adults
- Link: https://www.google.com/search?q=Vintage%20Champagne%20%26%20Small%20Plates%20at%2089%20Charles%20Beacon%20Hill%2C%20Boston

### 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.
- Location: Back Bay, Boston
- Cost: $$$
- Best for: Couples & Friends
- Link: https://www.google.com/search?q=Northern%20Italian%20Brunch%20at%20Contessa%20Back%20Bay%2C%20Boston

## 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.
- Venue: The Street Bar at The Newbury Boston
- Location: Back Bay, Boston
- Date: 2026-10-17 2:00 PM
- Cost: $$$
- Best for: Everyone
- Link: https://resy.com/cities/bos/the-street-bar

### 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.
- Location: Jamaica Plain, Boston
- Cost: $
- Best for: Everyone
- Link: https://www.google.com/search?q=Peak%20Canopy%20Walks%20at%20Harvard%27s%20Arnold%20Arboretum%20Jamaica%20Plain%2C%20Boston

## 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.
- Location: Salem, MA \(45 mins north\)
- Cost: $$
- Best for: Everyone
- Link: https://www.google.com/search?q=Salem%20Historic%20Harbor%20%26%20Haunted%20Happenings%20Salem%2C%20MA%20(45%20mins%20north)

### 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.
- Location: Jaffrey & Peterborough, NH \(2 hrs northwest\)
- Cost: $$
- Best for: Outdoor Lovers
- Link: https://www.google.com/search?q=Mount%20Monadnock%20%26%20Peterborough%20Countryside%20Jaffrey%20%26%20Peterborough%2C%20NH%20(2%20hrs%20northwest)

## Ready-made Boston, MA itineraries

- [A 3-Day Boston Weekend with Friends](https://wonderkit.app/itineraries/boston-ma/3-day-weekend-with-friends)
- [A Boston Fall Weekend with Friends](https://wonderkit.app/itineraries/boston-ma/fall-weekend-with-friends)
- [All Boston, MA itineraries](https://wonderkit.app/itineraries/boston-ma)

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