Autumn Family Bucket List: Jogging Stroller-Friendly Adventures

Man Pulling Wagon along trail

As the leaves turn to beautiful shades of red and orange and the heat of summer makes way for cool, crisp autumn air, it’s the perfect time to go outdoors and make unforgettable memories with your family. There are all kinds of seasonal activities that are both fun and stroller-friendly, giving families the perfect opportunity to spend time together while making the most of the season.  

We've put together an autumn family bucket list that’s packed with exciting stroller-friendly events and activities across the US and Canada. Bring your BOB Gear® jogging stroller or wagon along for the ride and enjoy these perfect outings that cater to both parents and kids! 


1. Apple Picking Adventures 

Why it’s perfect: Apple picking is a classic fall activity that the whole family can enjoy. It can be a great opportunity to teach your little ones about where our food comes from and the importance of taking care of our natural resources. Plus, you can take home some delicious apples for a healthy snack or fun fall baking. As you explore local orchards and farms, your BOB Gear jogging stroller can help you navigate the terrain with ease. 

Some Suggested Locations

Applewood Farm, Stouffville, Ontario: This farm offers apple picking, pumpkin picking, and a corn maze, making it the perfect destination for a family outing. 

Sky Top Orchard, Flat Rock, North Carolina the Blue Ridge Mountains, this orchard provides breathtaking views, fresh apple cider donuts, and plenty of space for strollers. 

Honey Pot Hill Orchards, Stow, Massachusetts: Known for its scenic orchards and fun maze, this location is great for families looking for a day of outdoor adventures. 

Tips: Arrive early to avoid the crowds and ensure you have ample space to stroll around comfortably. Don’t forget a rain cover for your stroller in case of unexpected weather changes! 

  

2. Pumpkin Patch Pictures and Hayrides 

Why it’s perfect: You can’t have fall without pumpkins and hay! Many farms offer photo opportunities, pumpkin picking, and hayrides, providing a fun and festive atmosphere for the whole family. Get some snapshots of your kiddos as they enjoy the festivities and pick out a pumpkin to take home for pumpkin carving.  

Some Suggested Locations

Bates Nut Farm, Valley Center, California: During their annual Pumpkin Patch event, this farm offers everything from hayrides and a straw maze to a petting zoo and mechanical bull rides. Don’t forget to stop by their famous store and take home some nuts, candy, or fudge.  

Schuster's Farm, Deerfield, Wisconsin: Find the perfect pumpkin for your jack-o-lantern, say hello to the animals, and grab a tasty treat from the Bakery Barn.  

Downey's Farm Market, Caledon, Ontario: Features an expansive pumpkin patch, farm animals, and wagon rides. 

Tips: Go during the weekdays to avoid the weekend rush. Dress your kids in bright, fall-themed outfits for the best photo ops. Most importantly, make sure your stroller is clean and ready for all-terrain adventures. 

3. Local Festivals 

Why it’s perfect: Local fall festivals are great for family bonding, offering a range of activities from food tastings to live music and games. The lively atmosphere and spacious settings make these events ideal for bringing your jogging stroller. Plus, you can support local artists, businesses, and restaurants by stopping by their booths.  

Some Suggested Festivals

 Warrens Cranberry Festival in Warrens, Wisconsin: Celebrate the cranberry harvest with marsh walking tours, arts and crafts vendors, and a parade on the final day.  

Fall for Greenville, Greenville, South Carolina: Enjoy one of the largest food festivals in the Southeast with stroller-friendly streets and a special kids’ area with rides and activities.  

 Pumpkinfest, Toronto, Ontario: Experience the best of autumn with rides, local food trucks, family-friendly entertainment, and more.  

Tips: Bring a picnic blanket and take breaks to enjoy the live entertainment and delicious food offerings. A stroller with a large storage basket will be handy for your purchases – just remember not to exceed the stroller’s weight limits.  

  

4. Hiking Family Trail Guide 

Why it’s perfect: Fall is a beautiful time to explore nature trails with your family. Many trails are jogging stroller-friendly, offering smooth paths and breathtaking fall foliage. 

Some Suggested Trails

Acadia National Park, Maine: Enjoy stunning coastal views and forest trails. 

Banff National Park, Alberta: Discover the Canadian Rockies with well-maintained trails. 

Great Smoky Mountains, Tennessee/North Carolina: Experience a variety of trails suitable for all skill levels. 

Tips: Check trail conditions before you go, pack plenty of water and snacks, and dress in layers to adapt to changing temperatures. Choose trails with rest areas to take breaks and enjoy the scenery. 

  

5. 5k Family Fun Runs 

Why it’s perfect: Participating in a 5k family fun run is a great way to stay active and enjoy the fall weather. Many events are designed to be family-friendly, allowing you to bring your jogging stroller along. Remember to put your stroller in jog mode and check the tire pressure before you take off – and don’t forget to use the wrist strap while running.  

Some Suggested Events

- Turkey Trot, Nationwide: Held in various cities, these events are often stroller-friendly and perfect for a pre-Thanksgiving workout. 

Monster Dash, St. Paul, Minnesota: A Halloween-themed run with costumes. 

Run for the Cure, Various locations in Canada: Support breast cancer awareness and enjoy a family-friendly run. 

Tips: Register early to secure your spot and receive a race packet. Dress in comfortable, breathable layers, and consider bringing snacks and water for the kids. Most importantly, have fun and enjoy the experience! 

These fall adventures offer the perfect opportunity to create lasting memories with your family. With your BOB Gear jogging stroller, you’re prepared to tackle any terrain and enjoy all the seasonal fun. Happy adventuring!