Fall in Boston and the Metrowest area is nothing short of magical. The air turns crisp, the leaves ignite in a blaze of color, and New England puts on its best show. From classic country fairs to charming city strolls, here's how to make the most of a fall in Metrowest and Boston with your family.
🍎 Apple Picking & Pumpkin Patches: A New England Tradition
While Boston has many charms, the sprawling orchards of the Metrowest are the essential destination for this classic fall activity.
Honey Pot Hill Orchards (Stow)
This is one of the most popular farms for a reason. With hayrides to sprawling orchards, a massive pumpkin patch, and friendly farm animals, it's a full day of fun.
💡 Pro-Tip: Their cider donuts are legendary. Go on a weekday morning to beat the weekend rush and have the place (mostly) to yourselves.
Lookout Farm (Natick)
Perfectly located for an easy trip from the city, Lookout Farm offers a slightly more streamlined experience with a charming train ride to the orchards.
🍺 Bonus: The outdoor taproom is also a fantastic perk for parents looking to relax while the kids enjoy the play area.
Smolak Farms (North Andover)
A bit of a drive, but worth it for the festival atmosphere. Smolak goes all-out with a corn maze, pumpkin displays, and activities that make it a true fall destination for the whole family.
🍂 Leaf Peeping & Family-Friendly Fall Walks
You don't have to drive for hours to see stunning foliage. Some of the best spots are right here.
In the Suburbs:
Callahan State Park (Framingham)
With miles of wide, relatively flat trails, this is a perfect spot for a family with a sturdy stroller and a four-legged friend.
Blue Hills Reservation (Milton)
For families with slightly older kids, the Skyline Loop trail offers a rewarding challenge with one of the best views of the Boston skyline you can get.
In the City:
Boston Public Garden & Beacon Hill
For the quintessential city fall experience, nothing beats a stroll through the Public Garden, followed by a walk through Beacon Hill's gaslit streets.
📸 Kids love watching the swan boats, and the pumpkin-decorated brownstones make for endless photo ops.
The Arnold Arboretum (Jamaica Plain)
This Harvard-owned landscape is a 281-acre treasure. It's a world-class collection of trees that puts on a spectacular, free foliage show.
🛴 The paved paths are perfect for strollers and little ones learning to ride their scooters.
🎪 Can't-Miss Fall Festivals & Events
Planning a fall outing with little ones? For gentle, toddler-friendly events, see our round-up: 7 Toddler-Friendly Metrowest MA Halloween Events. For couples planning weddings, here's how on-site care works and what it costs: Event Childcare for Weddings: How On-Site Care Works + What It Costs.
Regional Fairs:
King Richard's Faire (Carver)
Step back in time at this unique medieval fair, running weekends through late October. With knights, jousting, games, and giant turkey legs, it's a wonderfully different kind of fall festival.
Topsfield Fair (Topsfield)
As America's oldest agricultural fair, this early-October event is a must-do. From giant pumpkins and piglet races to classic midway rides, it's a full day of timeless family fun.
Boston Celebrations:
SoWa Open Market (South End)
This vibrant market of local artisans, farmers, and food trucks runs through October and takes on a wonderful harvest feel in the fall.
Boston Common Pumpkin Festival
Keep an eye on the city's schedule for this beloved tradition. Seeing hundreds of lit pumpkins float on the Frog Pond is a truly magical and not-so-spooky evening event for families.
🚗 Logistics: Best Times, Parking, and Stroller Tips for Boston Fall Fun
⏰ When to go
Weekday mornings or late afternoons for orchards and the Arboretum. Arrive at fairs right at opening to avoid lines.
🅿️ Parking intel
- Honey Pot Hill: On-site lots fill fast on weekends. Look for overflow signage.
- Lookout Farm: Dedicated lot near entrance. Train to orchards reduces walking.
- Arboretum: Street parking on Arborway and Centre St. Weekdays are easiest.
👶 Stroller-friendly picks
Callahan State Park wide trails. Arboretum paved paths. Public Garden and Beacon Hill sidewalks are fine, but Beacon Hill has hills and brick.
🍎 Restrooms and snacks
Bring water, wipes, and a simple snack kit. Most farms have portable restrooms. SoWa has plentiful food trucks; carry cashless options.
💡 Pro Tip
Build a 15-minute buffer for transitions and photo stops. For toddlers, plan one anchor activity plus a short playground stop.
An Extra Set of Hands for Your Fall Adventures
Planning these wonderful fall outings is one thing, but managing them with multiple little ones can be another. An experienced nanny can be a partner in adventure, making a trip to a crowded fair less stressful and a day of apple picking more joyful. Our caregivers love helping families make the most of every season.