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America’s Best Bike Rides

There are few activities that bring a family together quite like a bike ride. Whether it’s the beautiful scenery, the wind in your hair, or just the fact that you’re spending quality time together, it’s hard not to end the ride feeling like your whole family hasn’t just accomplished something special together. But these rides don’t have to stop once your own kids grow up and have a family of their own – in fact rides between grandparents and their grandkids can be even more amazing. So let’s hit the road, with the best bike rides in the country.

Boston – Emerald Necklace Trail

While the trail along the Charles River may get all the attention, we wanted to find a path that avoids some of the overcrowding and commotion you can find on that ride, especially during peak hours.

So instead, head slightly inland for a trail that explores some of the best parks the region has to offer, including many designed by famed landscape architect Frederick Law Olmsted (who also made New York’s Central Park!)

While the whole length is five miles (or 10 if you loop back around), there are many beautiful points along the way that you can use as a final destination, while still feeling accomplished.

Popular stops include The Fens (for which the famous ballpark is named), Jamaica Pond, and Arnold Arboretum.

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New York City – New Springville Greenway

America’s Best Bike Rides

While Manhattan has a lot to offer, it’s not our top pick for a family ride. For that, you should head to the borough with a less hustle n’ bustle, and a little more open space: Staten Island.

Freshwater Kills is practically brand new, and is an amazing success story in turning a former dump (literally) into a beautiful, sustainable amenity for the whole region.

New Springville Greenway is even newer, having just opened this summer. This ensures the path should be in top shape, with no bumps or potholes to slow your clan down. Plus, at only 3.3 miles, this ride should be easy enough to bring even the youngest grandchildren along with you.

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Philadelphia – Manayunk Bridge Trail

America’s Best Bike Rides

With its quaint row houses and laid back vibe, it’s sometimes easy to forget that Manayunk is a part of the city of Philadelphia. Riders will find this trail similarly easy-going, along with some great views and an interesting history that will keep the whole family interested.

Formerly a Pennsylvania Railroad, and then SEPTA, Train Bridge, this span served its last locomotive in 1986, and then sat empty for decades. A lively group of activists managed to secure funding to turn it into a bike path, with their vision finally opening to the public this fall. While the bridge itself is only 1/3 of a mile long, it hooks into a huge network of trails, guaranteeing you as much fun biking as you could ever want.

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Washington DC – The Capital Crescent

America’s Best Bike Rides

Our nation’s capitol also sports some capital green spaces. From the iconic National Mall, to the banks of the Potomac, DC is certainly blessed with a bounty of beautiful open space. But for this family friendly ride, we’re going to head away from the tourists, and out west towards Bethesda and Silver Spring.

Out there, you’ll find the Capital Crescent Trail. This 11 mile path follows the old route of the B&O railroad, meaning it’s thoroughly paved to guarantee a smooth ride. With lots of scenic stopping points throughout the city and its suburbs, this ride truly has something for any family.

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Miami – Commodore Trail

America’s Best Bike Rides

Miami may be famous for its beaches, but it sports some great places for biking as well. Whether it’s with a view of the ocean, the Miami River, or inland by the Everglades, Miami has some wonderful biking options for you and your grandsons and granddaughters.

The Commodore Trail affords you five miles of paved path, with nice water views, and travels through some of the city’s safest neighborhoods. While this path definitely helps you avoid some of the summer crowds that make biking in other areas tricky, there are a few places where you’ll want to look both ways as you cross the street. But other than that, it should be smooth riding!

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Chicago – Illinois Prairie Path

America’s Best Bike Rides

Were you worried we were only going to cover cities on the East Coast? Well fear not, because we have a great path for our Chicagoland readers too. We’ve found that some of the best bike paths are “rails-to-trails,” where an abandoned train line is converted into a smooth and beautiful path for biking on. Well luckily for Windy City citizens, the very first one of these to open in the country is in their own backyard – The Illinois Prairie Path.

While the first section opened in the late 1960s, the trail is still in great condition today, as volunteers lovingly maintain it over its many routes, which stretch from the western edge of Chicago into neighboring DuPage and Kane counties. Don’t expect to do the whole 61 miles in a single day; this path will have you coming back for more and more.

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Houston – Sandy Reed Memorial Trail

America’s Best Bike Rides

They say everything is bigger in Texas, and that applies to bike paths too! While some Texas paths can sprawl for miles, we decided to pick something a little more approachable.

The Sandy Reed Memorial Trail, in the heart of Buffalo Bayou park, affords both great greenery, set as it is along lush river banks, as well as great views of downtown Houston. The trail itself loops in at only 4.5 miles, making it a great ride for anyone and everyone.

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Dallas – Trinity Skyline Trail

America’s Best Bike Rides

We’re not taking sides in the famous Houston-Dallas rivalry, so we’ve picked out a trail for Dallasite grandparents that’s in every way the equal to the Houston trail. To match the Buffalo Bayou’s riverside trail, we picked a ride in Dallas’ Trinity River, which also sports some great views of Downtown.

The Trinity Skyline Trail is 4.6 miles of hard surface riding, basically matching the Houston ride inch-for-inch. With easy parking nearby and lots of wide spaces for stopping whenever you want, this is a great ride to take your grandkids on.

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San Francisco – Mission Creek Park

America’s Best Bike Rides

Heading to the West Coast, this region is famed for its natural beauty, making it hard to pick a favorite family-friendly ride in the SF Bay Area: there are just too many great options! While many hardcore bikers will head north to Marin, where mountain biking was first invented, we think grandmoms and granddads will prefer toting their tots to Mission Creek Park, which features great views of both the bay and the ball park.

While the park is located in San Francisco proper, the Mission Bay neighborhood is on the quieter side, guaranteeing a safe and simple ride for you and your whole family. Best of all, there’s both ample parking and good transit options nearby, making this an easy trail to get to.

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Los Angeles – Kenneth Hahn State Park

America’s Best Bike Rides

While this mega-city is famous for many things, those that know it well recognize it has a bevy of great outdoor spaces and trails. While some rides, like along Santa Monica Beach or Griffith Park, may be as famed as tinsel town’s celebrities, there are countless rides that fly right under the radar as well.

Tucked away in the hills above Culver City, Kenneth Hahn State Park has a number of loops and pleasant paths for riders of any level. This park not only avoids the crowds that can scare little ones on more popular paths, but there are also select spots with great views of the ocean, the mountains, and even Downtown.

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Hit the Trail

Ready to hit the trails with your grandkids?

Get to it, and let us know how you find the rides, or sound off with your own recommendations below! And if we haven’t gotten to a city you live in yet, fear not, because we’ll be coming up with more city recommendations in the days to come. And if you’re looking for a bike to help you keep up with the kiddos, we know just the place!