San Francisco

Crissy Field
This flat-paved trail offers photo-worthy views of the SF Bay and Golden Gate Bridge, beach access, picnic areas and historical landmarks. In the West Bluff area you’ll find the Warming Hut, which serves fresh pastries and a variety of drinks. The Torpedo Wharf is fun to explore while spying for seals. The close up views of the bridge here are impressive.
Location: Mason St., San Francisco

Golden Gate Park
We all know how much this park has to offer, though its size may seem daunting for a simple stroll. Don’t let that stop you from enjoying the wide, beautifully-landscaped trails with gardens and playgrounds along the way. Try entering at Stanyan and Haight and walking your way toward the coast.
Location: Stanyan and Haight, San Francisco

MacLaren Park 
From playgrounds to a lake, there is lots to explore in San Francisco’s second largest park. With over seven miles of scenic trails, the 2.7-mile Philosophers Trail is a good one for the stroller bunch. Take in the cityscape and ocean views, pack a snack and take a break at one of the many picnic areas.
Location: 100 John F. Shelley Dr., San Francisco

Lands End/Sutro Heights Park
Most of the main Coastal Trail can be done with wheels. Camino del Mar Trail is another one to consider. It is best accessed from the War Memorial parking lot, there are some stairs but still manageable and loops at the Legion of Honor. Stop by the visitors center near the main parking lot, there’s a cafe, restrooms and information plaques. Be sure to check out Sutro Bath ruins while there. For more stroller friendly trails with amazing ocean views, stroll across to Sutro Heights Park and explore the area that was formerly Sutro Estates and Gardens.
Location: 680 Point Lobos Ave., San Francisco

The Presidio
The Presidio is super stroller friendly with tons of trails for exploring and amazing views of the San Francisco Bay. Download this guide for an interactive experience while hiking on the Ecology Trail or Anza Trail. The guide points out native plants and animals, talks about the history of The Presidio and helps kids explore the area while hiking.
Location: 210 Lincoln Boulevard on the Presidio’s Main Post, San Francisco

East Bay

Point Pinole Regional Shoreline
This easy hike is nearly all flat, with some gentle hills, picnic areas and a children’s playground. You don’t even have to walk to the fishing pier—a shuttle will pick up guests from the parking lot. Over 100 species of birds, myriad wildflowers in season and you could go fishing at the pier.
Location: Location: 5551 Giant Hwy., Richmond

Redwood Regional Park
The paved trail here is short and sweet at one mile long. It's perfect to get a dose of nature without having to strap a day’s worth of baby gear on your back. Bring the stroller for the baby and the bicycle for the toddler, and do two miles round-trip on the Stream Trail. Along the way, enjoy a canopy of redwood trees (bring sweaters for the shade) and a playground.
Location: 7867 Redwood Rd., Oakland

Lafayette Reservoir
Take the Lakeside Nature Trail—a paved, 2.7-miles around the Lafayette Reservoir. It’s mostly flat and shady, with pretty views of the hills and water. When you’re ready to break from walking, choose a table on the east lawn, where the playground will keep little squirm-balls busy. Remember to bring $6 for parking (exact change only), or to bring plenty of quarters for metered, two-hour parking.
Location: 3849 Mt. Diablo Blvd., Lafayette

Mount Diablo State Park
This rugged mountain may not be the first to come to mind, but it does have its gentler points. Near the summit, the Mary Bowerman Interpretive Trail is quite doable at less than a mile long, with access to the Summit Museum and lots of picnic tables.
Location: Summit Road off of Southgate, Danville

Iron Horse Regional Trail
Here you'll find 32 miles of paved multi-use trails that are perfect for cycling, scootering or pushing strollers. Mostly flat, the trail passes through various parks. If you park at Hillgrade Avenue and head South, you’ll pass by some horses and chickens. Perfect to keep the kids excited, you can bring carrots and feed the horses.
Location: Hillgrade Ave., Dublin

Peninsula

Coyote Point Recreation Area
Coyote Point has several stroller-friendly trails to choose from. Enjoy views of the San Francisco Bay, airplanes at SFO, Eucalyptus groves and more. Dip your feet into the beach and let the little ones run wild at the Magic Mountain Playground. Park on Airport Blvd. to enter park through Bay Trail, or bring $6 for main park entrance.
Location: 1701 Coyote Point Dr., San Mateo

Sawyer Camp Segment-Crystal Springs Regional Trail
This is a popular, three-mile segment, within the Crystal Springs Regional Trail. It is wide and paved with serene views of Crystal Springs Reservoir. Your little trekkers will love seeing the native wildlife and the amazing 600+ year old Laurel tree. There are restrooms and picnic tables a long the way but no drinking fountains. Also: no dogs allowed.
Location: Skyline Blvd & Crystal Springs Rd., San Mateo

Crystal Springs Regional Trail
With beautiful views of the reservoir and paved paths, this hike is super kid friendly. Restrooms are found near the Pulgas Water Temple side. Carry your own water.
Location: Skyline Blvd & Crystal Springs Rd, San Mateo

Mori Point
Most of the trails here are doable with stroller. Some are inclined and bumpy but worth the awesome ocean views. Keep your eyes open for blooming wild flowers, San Francisco Garter snakes and California red-legged frogs, both threatened native wildlife that thrive in the area. Accessible trail off of Old Mori Rd. has restrooms near by. Dress in layers as it gets pretty windy.
Location: Mori Point Rd. and Bradford Way, Pacifica

Purisima Creek Redwoods Preserve
The .25 mile, flat Redwood trail, loops around towering redwoods and is perfect for strollers. There are restrooms and picnic tables nearby. Some of the other trails are stroller accessible with some unpaved inclines that are done best with a carrier. You’ll find a creek, wildflowers, amphibians and great views of Half Moon Bay. Parking is limited.
Location: Main entrance: Skyline Blvd. (Highway 35), 4.5 miles south of highway 92. Redwood trail: 6.5 miles south of Highway 92, Half Moon Bay

Stanford Dish
This gorgeous hike takes you up into the rolling hills near the famed satellite dish that you can see from 280. Park at Junipero Serra Blvd. and Stanford Ave. and you can catch the paved trail from here. The trail makes a loop of 3.65 miles and is fully exposed and at times can be really steep. Best time to visit is on the weekdays as the trail can get busy with hikers on the weekends. Use the bathroom before you go and carry your water as there are no facilities on site.
Location: Junipero Serra Blvd. and Stanford Ave. in Palo Alto

South Bay

Rancho San Antonio Preserve
There are 24 miles of trails in this preserve, it’s free and has tons of parking. The easy one-mile trek from the main parking lot to the Deer Hollow Farm, is a popular one for families with strollers. Go early on the weekends as the parking lot does fill up. 
Location: 22500 Cristo Rey Dr., Los Altos

Santa Teresa County Park
The park has 17 miles of unpaved trails, most are fine for strollers. The Joice and Norred trails offer great views of San Jose and a look at the historic Bernal-Gulnac-Joice Ranch. The Pueblo Day Use Area is a popular stop—there are restrooms, picnic tables and horseshoe pits. There is lots of wildlife in the area, including grazing cows and calves. Bring $6 for parking.
Location: 260 Bernal Rd., San Jose

Fremont Older
This hundreds-of-acres large preserve includes miles of wide, pleasant trails. Enter the park gate at Prospect Road for a view of Silicon Valley, or take the Seven Springs Loop to enjoy the oak groves and search for lizards in the meadow. This trail can be hilly and is popular with bicyclists.
Location: Prospect Rd. off of De Anza Blvd. in Cupertino

Picchetti Ranch Preserve
The 3.7 miles of trails with forested canyons of madrone, coast live oak and California bay provide shade on a warm day. The Zinfandel Trail ducks into the forest, crossing seasonal creeks. The Bear Meadow Trail invites a leisurely walk to a small pond, making a pleasant setting for a picnic and singing some songs. 
Location: 13100 Montebello Rd, Cupertino

Marin/North Bay

Tennessee Valley Trail
This flat, paved and dirt trail, begins at the main parking lot. The 3.4-mile, round trip hike, will take you through coastal hills and habitat to native wildlife. At mid point, you can take the low or main trail. The main is steep through a hill and the lower, to the left, remains flat and simple. There’s a pit toilet at half way point, before reaching the rewarding Tennessee Beach. At low tide you can see remnants of the Tennessee shipwreck, after which the trail is named.
Location: at the end of Tennessee Valley Rd., Mill Valley

Blackie’s Pasture
This trail, which begins at Blackie’s Pasture and continues on to downtown Tiburon, is flat and easy. Stroll along slowly, enjoy the views of the Bay, stop at the playground and read about the history of the area with the help of some reading plaques along the way.
Location: Intersection of Trestle Glen Rd., Tiburon

Verna Dunshee Loop Trail
At less than a mile long, this is as flat and paved as you can get on the Sleeping Lady and the go-to for the stroller set who want to climb a mountain. It’s still Mt. Tam, however, so beware of some narrow passes and steep outlook points. Find the Verna Dunshee Loop on Mt. Tam’s East Peak, by the visitor center ($8 to park), and look forward to a front-row view of the Pacific Ocean and SF Bay.
Location: East Ridgecrest off of Pantol, Mill Valley

Corte Madera Creek Path, Greenbrae
A favorite with locals on bikes, this wide, easy path begins with a neat playground (Hal Brown Park) sectioned off for preschoolers and for older kids. If you can convince the kids off the climbing structure, you can walk with them from here all the way into Ross.
Location: Bon Air Rd., Greenbrae

China Camp State Park
Wheelchair accessible with beautiful views of San Pablo Bay, this one is great to let the young ones stretch their legs as bikes are not allowed. Wildflowers are abundant and placards along the way provide information on the flora and fauna. Park along San Pedro Road at the north end of China Camp and head to the Turtle Back Nature Trail for some shade in the hotter months.
Location: 101 Peacock Gap Trail, San Rafael