The Ultimate Guide to Kid-Friendly Holiday Events in Boston & MetroWest (2025)

Boston Common Tree Lighting

• When: Late November (check official date)
• Time: Typically 6:00 PM ceremony
• What to expect: The state's official Christmas tree (a gift from Nova Scotia) is lit with great fanfare, including performances, caroling, and appearances by special guests
• Age range: All ages, but best for kids 3+
• Insider tips:
  • • Arrive by 5:15 PM to secure a good viewing spot
  • • Dress warmly—you'll be standing outside for 45+ minutes
  • • Park at Boston Common Garage or take the T (Park Street station)
  • • After the lighting, stroll down Commonwealth Avenue Mall to see the iconic lit trees lining the pedestrian path
• Stroller-friendly: Yes, but crowded
• Cost: Free

Wellesley Holiday Lighting

• Where: Wellesley Town Hall
• When: Early December (check town calendar)
• What to expect: Tree lighting, caroling, hot cocoa, and sometimes a visit from Santa
• Best for: Families with young children who need a shorter, less overwhelming event
• Cost: Free

Natick Center Holiday Stroll

• Where: Natick Common
• When: Early December, typically first Friday
• What to expect: Tree lighting, holiday market, live entertainment, horse-drawn carriage rides
• Insider tip: The carriage rides are first-come, first-served and go quickly
• Cost: Free (carriage rides may have a small fee)

Concord's Holidays in the Village

• Where: Monument Square
• When: Early December weekend
• What to expect: Multiple days of festivities including tree lighting, caroling, craft fair, and Jingle Bell Run
• Best for: Making a full afternoon/evening out of it
• Cost: Free admission, some activities ticketed

Needham Holiday Celebration

• Where: Needham Town Common
• When: Check town website for specific date
• What to expect: Tree lighting, carolers, Santa arrival, and community bonfire
• Cost: Free

Newton Village Day & Tree Lighting

• Where: Newton Centre
• When: Early December
• What to expect: Multiple villages celebrate—check Newton's official site for all locations
• Cost: Free

Lookout Farm (Natick)

• When: Multiple December weekends
• Tickets: $25-35 per person, children under 2 often free
• Bonus: Access to holiday activities on the farm, wagon rides, visit the animals
• Book by: Mid-November (these sell out first)
• Best for: Toddlers through age 8
• Website: lookoutfarm.com

Boston Park Plaza

• When: Multiple December weekends
• Tickets: $50-65 per person
• What's special: Elegant setting, professional photographer, upscale buffet
• Best for: Families who want a more formal experience
• Book by: Early November

Local Options to Search:

• Your town's recreation department (many host them at community centers)
• Local country clubs (often open to non-members for holiday events)
• Fire stations (some host pancake breakfasts with Santa)
• Libraries (occasionally offer smaller-scale events)
• Local restaurants (especially family-friendly spots like Bertucci's, Tavern in the Square)

💡 Search tip: Google "[Your Town Name] Breakfast with Santa 2025" starting in early November. Join your local moms' Facebook group—they're typically the first to share when tickets go on sale.

What to bring:

• Your phone for photos (though professionals are usually there)
• A backup outfit for toddlers (pancakes + syrup = mess)
• Your child's Santa letter if they've written one

Stone Zoo "ZooLights" (Stoneham)

• When: Late November through early January, typically Wednesday-Sunday evenings
• Time: 5:00-9:00 PM (last entry 8:00 PM)
• Cost: $16-24 depending on age/day
• What to expect: Over a million lights transforming the zoo, animal viewing (some indoor exhibits), s'mores stations, holiday music
• Duration: Plan for 1.5-2 hours
• Age range: All ages, perfect for 2-10
• Insider tips:
  • • Buy tickets online in advance—weekends sell out
  • • Go on a weeknight for smaller crowds
  • • Dress very warmly—you're outside the entire time
  • • Strollers are allowed but the hilly terrain can be challenging
  • • Hit the bathrooms before you start (limited facilities mid-route)
• Best photo op: The glowing animal sculptures near the entrance
• Website: zoonewengland.org

La Salette Shrine Festival of Lights (Attleboro)

• When: Thanksgiving through early January, nightly
• Time: Dusk - 9:00 PM
• Cost: Free (donations appreciated)
• What to expect: Drive-through or walk-through display with over 300,000 lights, religious and secular displays
• Duration: 30-45 minutes driving, 60+ minutes walking
• Best for: Families who want a free option or prefer to stay in the car
• Insider tip: Go on a weekday evening to avoid traffic backups
• Distance from MetroWest: About 45 minutes, worth the drive

Bright Nights at Forest Park (Springfield)

• When: Late November through early January
• Cost: $25 per carload weeknights, $30 weekends
• What to expect: 2.5-mile drive-through with elaborate displays
• Why it's worth the drive: One of New England's premier holiday light shows
• Insider tip: Bring hot chocolate and holiday music—it's a 30-40 minute drive-through

Frog Pond on Boston Common

• When: Mid-November through mid-March (check specific dates)
• Hours: Vary by day, typically 10 AM - 9 PM
• Cost:
  • • Adults: $10
  • • Kids 13 and under: $6
  • • Skate rental: $15
  • • Lockers: Small fee
• What's special: Skating in the heart of Boston with the city skyline as your backdrop—quintessential New England
• Age recommendation: Best for ages 5+ (younger kids can do it but may struggle)
• Insider tips:
  • • Weekday mornings are least crowded
  • • Saturday/Sunday afternoons and evenings get very busy
  • • Skate helpers/trainers available for beginners
  • • The Frog Pond Café sells hot chocolate and snacks
  • • Lockers are worth it—you don't want to carry coats while skating
  • • Parking: Boston Common Garage or take the T to Park Street
• Stroller parking: Available in designated areas
• Website: bostonfrogpond.com

Larz Anderson Park Skating Rink (Brookline)

• When: December through February (weather dependent)
• Cost: Free admission, skate rentals available
• What's special: Outdoor rink with a community feel, less chaotic than Frog Pond
• Best for: Families who want a more relaxed experience

Skating tips for young kids:

• Consider "penguin helpers" (skating aids) if available
• Dress in layers they can move in (snowpants can be restrictive)
• Helmets are smart for beginners
• 20-30 minutes is plenty for first-timers
• Bring extra gloves—they will get wet

The Gold Standard: Boston Ballet's "The Nutcracker"

Boston Opera House

• When: Thanksgiving weekend through late December
• Tickets: $35-$200+ depending on seats and date
• Runtime: About 2 hours with intermission
• Age recommendation: 5+ (some 4-year-olds can handle it)
• What makes it special: World-class production, spectacular sets and costumes, live orchestra
• Insider tips:
  • • Matinee performances are more kid-friendly
  • • Book balcony seats for first-timers (less pressure to sit perfectly still)
  • • Explain the story beforehand—kids who know what to expect engage more
  • • Dress up! It makes it feel extra special
  • • Intermission: 15-20 minutes for bathroom breaks
  • • Many families make this an annual tradition starting around age 5-6
• Book by: October for best seat selection
• Website: bostonballet.org

More Accessible Options

• "Black Nativity" (Boston): Gospel-infused retelling of the nativity story. Best for families looking for a more interactive, joyful performance. Age range: 4+
• Community Theater Productions: Many local theaters produce holiday shows perfect for families. Check Wellesley Players, Needham Community Theatre, Newton South High School performances. Often more affordable ($10-25) and kid-friendly lengths (60-90 minutes)
• "A Christmas Carol" Readings/Productions: Various theaters across the region. Typically early-mid December. Great for kids 7+ who can follow a story
• Story Time with Santa at Local Libraries: Free events throughout December. Perfect for toddlers and preschoolers. Check your library's calendar in late November

Boston Holiday Market (SoWA)

• When: Weekends in December
• What: Local artisans, food vendors, holiday shopping
• Best for: Parents who want to shop while kids enjoy the festive atmosphere
• Kid appeal: Hot chocolate, sometimes entertainment

Faneuil Hall Marketplace

• When: All month, special events on weekends
• What: Holiday decorations, street performers, shops
• Kid highlight: The big tree, Blink! light show
• Insider tip: Can be very crowded on weekends

Local Craft Fairs

Every town has them in December. Check: Church bulletins, community center calendars, town Facebook pages. Often have craft activities for kids.

Edaville Railroad "Christmas Festival of Lights"

• Where: Carver, MA (about 50 minutes from MetroWest)
• When: Late November through December
• What: Vintage train rides through 150,000+ lights, Santa's village, train-themed amusement rides
• Cost: $35-45 per person
• Duration: Plan for 2-3 hours
• Age range: Perfect for 2-8
• Worth the drive: Yes, especially for train-loving kids
• Insider tip: Weekday evenings less crowded

Jordan's Furniture Enchanted Village (Avon)

• When: Day after Thanksgiving through December
• What: Free elaborate holiday display with moving scenes, plus Santa photos
• Cost: Free admission, photos have various packages
• Why it's special: The Enchanted Village is a Boston tradition since 1958
• Best for: All ages
• Insider tip: Weekday mornings are quietest

Other Options:

• Local Photography Studios: Many offer mini sessions with Santa in November/December. Search "[Your Town] Santa photos" or "Santa mini sessions MetroWest". Often higher quality than mall photos and more relaxed setting.
• Mall Santas: Natick Mall, Chestnut Hill Mall, Burlington Mall all have Santa. Book time slots online to avoid lines. Weekday mornings right when mall opens = shortest wait.

Wilson Farm (Lexington)

• Holiday workshops throughout December
• Cookie decorating, wreath making, ornament crafts
• Check website for schedule and registration

Other Craft Options:

• Pottery Painting Studios: Create holiday gifts or ornaments. Most towns have a local option (search "paint your own pottery [town name]"). Great for ages 4+
• Gingerbread House Decorating: Many bakeries and cafes offer workshops. Clear Flour Bread (Brookline), local community centers
• Library Programs: Free craft sessions throughout December. Story times with holiday themes. Check your library calendar weekly

Boston Children's Museum

• Special holiday programming throughout December
• Countdown to Noon on New Year's Eve (daytime celebration)
• Best for: Ages 0-10

Museum of Science

• Holiday-themed shows in the Planetarium
• Special exhibits often debut in December
• Best for: Ages 4+

Peabody Essex Museum (Salem)

• Often has elaborate holiday displays
• About 30-40 minutes from MetroWest
• Best for: Families with older kids (8+) who appreciate art/history

Advent Calendar Countdown

Daily small activities leading to Christmas

Ideas: holiday movie, bake cookies, drive to see lights, write letter to Santa, make ornaments

Holiday Movie Marathon Weekends

Classic rotation: Elf, The Polar Express, Home Alone, Rudolph, A Charlie Brown Christmas

Make it special: popcorn, hot chocolate bar, pajamas, blanket fort

More At-Home Ideas:

• Baking Together: Cookie decorating party, gingerbread house construction, holiday treat bags for neighbors/teachers
• Neighborhood Walks: Evening strolls to see decorated houses, sing carols as you walk, free and exhausts little legs before bedtime
• Letters to Santa: Write and "mail" them (USPS has a Santa letter program). Make it an event with special paper and hot chocolate

Company Holiday Parties (our #1 booking reason in December)

Remember that corporate party blog post? On-site childcare removes every barrier:

• Parents can actually attend and enjoy themselves
• No scrambling for last-minute sitters
• No paying premium rates for Saturday evening care
• Kids are safe, happy, and nearby

Holiday Shopping Sans Kids

• Book 3-4 hours on a weekend afternoon
• Actually browse and think about gifts
• Try on clothes for holiday events
• Shop without "Can we leave yet?" every 10 minutes

What Makes HavenFlex™ Different for Holiday Childcare

• RN-Vetted Professionals: Not random teenagers from a neighborhood app—experienced, background-checked, insured W-2 employees who bring structure and professionalism.
• Holiday Activity Planning: Our caregivers come prepared with age-appropriate holiday activities: holiday crafts and coloring, Christmas story time, age-appropriate holiday movies, outdoor play (weather permitting), baking or decorating cookies (if you prefer)
• Flexible Booking: Book for just 2-3 hours or a full day. In-home care or on-site event childcare. One-time or recurring (same caregiver available)

December 2025 Booking Information

Most Requested Time Slots (Book ASAP):

• Weekends in Early-Mid December (Saturday/Sunday afternoons)
• December 31st (evening)
• Wednesday afternoons (half-day school weeks)
• Week of December 22-29 (school break, parents working or prepping)

Current Availability: As of early November, we still have good availability, but historically our December calendar is 70% full by Thanksgiving week.

How to Book:

1. Call or text: (774) 292-4600 (fastest response)
2. Email: info@nurturehavennannies.com
3. Online: Check real-time availability and book

Early November (NOW):

• Check town websites for tree lighting dates
• Book "Breakfast with Santa" tickets as soon as they go on sale
• Reserve Nutcracker tickets if interested
• Book HavenFlex™ care for company holiday party
• Put Stone Zoo ZooLights on calendar

Mid-November:

• Book any remaining childcare dates you'll need
• Buy Frog Pond skating tickets for a specific date
• Check library calendars for holiday programming
• Plan which neighborhoods to drive through for lights