At the end of each year, I typically have everyone in the family rank their favorite places & activities of the year. In 2020 we didn’t really travel and instead spent a lot of time outside hiking. So this year, I stuck to ranking hikes, all of which are in California.

Everyone had to rank each hike on a scale of 1-10. All 5 of us didn’t go on every single hike, but each hike has at least 1 kid’s input. I’ll give details about each hike and why it falls at the top of our list.

#10 – Rancho Corral de Tierra

Moss Beach

I added this hike to my list of stunning coastal winter hikes and it turns out my family agrees!

Details

  • Distance: 4 miles
  • Elevation: 1500’ gain
  • Our rating: Moderate
  • Dog Friendly: Yes
  • Parking: Free on the side of the road (no designated lot)
  • Restrooms: No (secluded bushes: yes)
Found this swing at the top of the trail! You can see Pillar Point off in the distance. Rancho Corral de Tierra. Moss Beach, California
Found this swing at the top of the trail! You can see Pillar Point off in the distance.

Our Rating: 7.25/10

4 of us did this hike (Mike & I plus our 13 & 10-year-old, and our dog). We went on a beautiful day in late December. The trailhead is a little bit tricky to get to. We parked in the designated area at the intersection of Etheldore Street and Ranch Road in Moss Beach. Then we walked up Ranch Road past an equestrian center, at the end of the road we went through a gate and veered right through a little farm area with horses, llamas & goats, and followed the small signs towards Spine Ridge Trail. Once on the trail, we headed straight up and before long we were able to see the iconic golf ball at Pillar Point in Half Moon Bay. The views were gorgeous and I’ve heard that on a foggy day this trail takes you above the fog.

I enjoyed this hike because of the great workout and we had it entirely to ourselves. The kids liked it because it was dog friendly, they liked walking by the horses & farm at the beginning, but the big draw of this hike was the swing at the top. We did not know about the swing until we came upon it and who knows if it will still be there if we go back. There was a bit of complaining about the elevation gain on the way there, but they seemed to forget all about that once they saw the swing. And of course, the way back down was a breeze!

Afterward stop at Moss Beach Distillery which has a dog-friendly firepit patio, gorgeous ocean views, great food & a haunted past! 

#9 – Headlands Trail

Russian Gulch State Park, Mendocino

Details

  • Distance: ~1 mile
  • Elevation: negligible
  • Our rating: Very Easy
  • Dog Friendly: No
  • Parking: $8 entrance fee to the park
  • Restrooms: Yes
Looking out at Russian Gulch Bridge from the Headland's Trail. Russian Gulch State Park. Mendocino, California
Looking out at Russian Gulch Bridge from the Headlands Trail

Our Rating: 7.4/10

After passing through the park Entrance Station and paying an $8 fee, we took the first right towards the Headlands Trail and parked in the first dirt lot. This let us out right by the overlook to the Russian Gulch Bridge. There were lots of picnic tables here (we should have brought lunch) and we just admired the bridge for awhile. Then we followed the path west along the bluff past another parking area out onto a bluff with GORGEOUS views and extremely steep drop-offs. Aside from the ocean views, there was also a huge sinkhole (Devil’s Punchbowl) which was protected by a fence so we couldn’t get too close.

This was Mike’s favorite hike of the year. For such a short hike it packed a huge punch with the views, bridge, rugged coast, and the sinkhole. Our daughter said she would have rated this hike higher, but it was too short. There are plenty of other nearby trails within the park to extend this hike and make it longer. Instead, we drove down to the beach at the base of the bridge where we tossed around a football & frisbee and searched for treasures in the sand.

All 5 of us went on this hike during a weekend trip to Mendocino. Read more about this hike and our trip here.

#8 – Cowell-Purisima Trail

Half Moon Bay

Details

  • Distance: 7.2 miles (out & back)
  • Elevation: Flat
  • Our rating: Easy
  • Dog Friendly: No
  • Parking: Free at both the northern & southern trailheads
  • Restrooms: Yes
Enjoying the bluff views along the Cowell-Purisima Trail. Half Moon Bay, California
Enjoying the bluff views along the Cowell-Purisima Trail

Our Rating: 7.5/10

Just my 10-year-old and I did this hike over winter break – we loved it and can’t wait to bring the rest of the family back to this trail. We parked at the northern trailhead at Cowell Ranch Beach. The lot is small and we ended up along the side of Highway 1. Take the path about half a mile towards the beach, just before the overlook there’s a gate to the left where the trail begins. The trail is wide, flat, and mostly gravel – it’s great for jogging strollers & bikes. It meanders along a coastal bluff where there are pastures on one side and sweeping ocean views on the other. We crossed several pedestrian bridges and kept a look out for seals, whales, and hawks. About 2 miles into the hike, the trail briefly turns to dirt as it descends into a little valley and crosses Purisima Creek. Here we saw quite a few banana slugs along the trail! We turned around after 2.5 miles as we started the hike later in the day and needed to get back before the sun set, but next time we’ll hike the entire way. Save time at the end to hang out at Cowell Ranch Beach!

Until recently, this trail was only open on weekends & holidays – now it’s open every day of the week which may help reduce weekend crowds! More on Cowell-Purisima Trail here.

#7 – Devil’s Slide Coastal Trail

Pacifica

Details

  • Distance: 2.6 miles (out & back)
  • Elevation: 436’ gain
  • Our rating: Easy
  • Dog/Bike/Stroller/Equestrian Friendly
  • Parking: Free at both the northern & southern trailheads
  • Restrooms: Yes
Devil's Slide Trail is converted from an old segment of Highway 1 - so you feel like you're walking down the middle of the road! Pacifica California
Devil’s Slide Trail is converted from an old segment of Highway 1 – so you feel like you’re walking down the middle of the road!

Our Rating: 7.6/10

Anyone who has lived in the Bay Area for a while will likely remember hearing traffic reports announcing: “Highway 1 closed at Devil’s Slide”. Highway 1 which hugs the California coastline is arguably one of the most beautiful drives in the world. The views along the bluffs are stunning and the hair-raising turns on the edge of the cliff are nerve-wracking. This part of the highway first opened in 1937 and 3 years later was buried under fallen rocks. From this point on, at least once a decade, the road would close due to landslides and erosion. Devil’s Slide is made up of sedimentary rock which is extremely unstable and prone to crumble. In 1995 the road closed for 6 months which prompted a call to action: divert the highway by boring two new tunnels through San Pedro Mountain. When this was completed in 2013, the old Devil’s Slide segment became a multi-use trail.

All 5 of us hiked this in July on a gorgeous clear day. We loved the unique aspect of hiking down the old roadway and taking in all the views. We all found the history of this roadway fascinating and loved seeing all the visible layers of mud and sand lifted up from the ocean floor over millennia by shifting tectonic plates. Additionally, there are multiple informational signs describing the geology, marine & plant life as well as various lookout points with telescopes. Dog-friendly, under 3 miles, easy with minimal elevation gain, gorgeous views, and educational – this hike was a winner all around!

Just one quick note: my sister recently did this trail with her 5- and 2-year-old daughters on scooters. She was by herself and found it tough to manage both of them as the slope of the trail is steep in places. So maybe scootering here is better for kids more comfortable on scooters or keep an adult:child ratio of 1:1!

More on Devil’s Slide here.

#6 – Lands End Trail

San Francisco

Details

  • Distance: 3.5 miles (out & back)
  • Elevation: 500’ gain
  • Our rating: Moderate (there are a lot of stairs, especially if you take the Mile Beach offshoot)
  • Dogs on leash
  • Parking: Free at Lands End Lookout
  • Restrooms: Yes, at Lands End Lookout
Land's End Rock Labyrinth. San Francisco, California
Land’s End Rock Labyrinth

Our Rating: 7.75/10

We LOVE this hike right in the middle of San Francisco! The weather can be hit or miss (we’ve hiked it on both cold foggy days and warm sunny days), but the views and history of this trail are fantastic anytime. We’ve hiked here with both our 10 and 13-year-old and our dog.

This trail has so many engaging features and something of interest for all from amazing views of the Golden Gate Bridge & Marin Headlands, a rock labyrinth, Mile Rock Beach, shipwrecks, the Cliffhouse and Sutro Baths to Camera Obscura. Read more about why we love this hike here.

#3 (3-way Tie) – Kehoe Beach Trail

Point Reyes

Details

  • Distance: 2.5 miles (out & back)
  • Elevation: Flat
  • Our rating: Easy
  • Dogs on leash
  • Parking: Free on the side of the road
  • Restrooms: Yes at the trailhead
Where the trail meets the beach! Point Reyes National Seashore. California
Where the trail meets the beach!

Our Rating: 8/10

We chose this hike in Point Reyes because it leads to a dog-friendly beach. My 10 and 13-year-old and I went here during the week in July and it was overcast and chilly. The trail was very easy – the hardest part was climbing over the sand dunes at the end to reach the beach. Kehoe Beach is huge and was mostly deserted aside from 3-4 other groups. I love the beaches up here as they feel so rugged – we saw lots of kelp, seaweed, jellyfish, and crab all over the beach. The kids loved running around the beach and chasing waves with our dog. The trail was nice and we felt like we had it to ourselves, but the beach was the real winner here. While we were here, we had plans to see some other Point Reyes highlights like the cypress tunnel and shipwreck, but once we got here the kids didn’t want to leave so we only made it to this beach. We picked up sandwiches at Whale of a Deli in Point Reyes Station and ate them on the beach.

From the peninsula, this is a long way to drive for a hike, so I recommend getting an early start and planning to spend the whole day in the area.

#3 (3-way Tie)- Dipsea Trail

Mill Valley

Details

  • Distance: 3.6 miles
  • Elevation: 948’
  • Our rating: Moderate
  • No dogs
  • Parking: $10 at the Pantoll parking area
  • Restrooms: Yes at trailhead
Looking south towards San Francisco from the Dipsea Trail on Mt. Tam. Mill Valley, Marin County California
Looking south towards San Francisco from the Dipsea Trail on Mt. Tam

Our Rating: 8/10

I started hiking the Dipsea Trail with my dad when I was a kid and it still holds my #1 spot for Best Bay Area hike (best hike ever? Definitely the Kalalau Trail along the Na Pali Coast in Kauai). Not surprisingly, the Dipsea was my top-rated hike of the year and I’ll take #3 overall from the rest of my family.


There are many variations of this hike depending on the difficulty and mileage you want to take on (ranging from a few miles to 15+). This summer I took the boys on a Dipsea introduction hike. I chose one of the easiest routes, but it’s still a moderate hike with many stairs and drop-dead gorgeous views. It was warm and clear and we had amazing views. I always bring layers when hiking in Marin – even in the summer because the weather can change quickly & suddenly.

We began at the Pantoll parking area and hiked the Old Mine –> Dipsea –> Steep Ravine loop. I was not used to starting from this spot so we actually hiked it backward which works, but I recommend going in the order above. The Dipsea trail is exposed with little shade which makes it better for the downhill portion. This way you also hike facing the Pacific rather than with your back to it. The Steep Ravine portion is like taking a step back into time with redwoods, ferns, and waterfalls. There are a ton of steps, bridges, and even a ladder to climb. As a kid, this ladder always stood out to me – I loved it and looked forward to it. When I had the kids rank our hikes, the boys asked “is that the hike with the ladder?”

I’m looking forward to going back this year and hiking more – maybe starting from Stinson Beach and making a larger 6 mile loop. One day, I’ll conquer the Double Dipsea.

#3 (3-way Tie)- Tahquitz Canyon Trail

Palm Springs

Details

  • Distance: 1.7 miles
  • Elevation: 328’
  • Our rating: Easy trail overall, but Moderate due to the summer heat
  • No dogs
  • Parking: Free, but there is an entrance fee to hike ($12/adult; $6/child 6-12; under 6 Free, as of February 2021)
  • Restrooms: Yes at trailhead
Swimming at Tahquitz Falls. Palm Springs, California
Swimming at Tahquitz Falls

Our Rating: 8/10

Tahquitz Canyon is in the Agua Caliente Indian Preserve in Palm Springs. The hike to the falls is an easy 1.7 miles round trip hike to a 60-foot waterfall with a large swimming hole!

All 5 of us did this hike at the end of June. IT. WAS. HOT. The trail is accessible beginning at 7:30am. We were there at 8am (which is an amazing feat with two teens!) and it was already 90 degrees. The ranger station monitors that every hiker is carrying at least 32 oz of water. If you go in the summer – go early! – not only to avoid the hottest part of the day but also this is a well-trafficked hike and by the time we got to the waterfall there was already a decent number of people there. The waterfall creates a large swimming hole with cold water and we immediately jumped in with our clothes on! We swam all around under the falls. It was amazing! We also saw a few bighorn sheep along the way! This was Kate’s favorite hike of the year!

I don’t like crowded hikes, but I think this one is worth it. Even though it was hot, starting the hike early and getting to experience the refreshing swimming hole was so fun & memorable. We were lucky the waterfall was still flowing – my advice is to check recent reviews on Alltrails or another review site to make sure it’s flowing before you go. There’s nothing worse than promising your kids a waterfall and then not being able to deliver. In winter/spring the weather is cooler and the waterfall has a better chance of flowing, but it would be too cold to swim. Read all the details of this hike here.

#2 – Wilbur’s Watch

Pescadero

Details

  • Distance: 2 miles
  • Elevation: 260’
  • Our rating: Easy
  • No dogs
  • Parking: Free at the trailhead
  • Restrooms: Yes at trailhead
Taking advantage of the telescope to check out the views at the top of Wilbur's Watch. Pescadero, California. San Mateo County
Taking advantage of the telescope to check out the views at the top of Wilbur’s Watch

Our Rating: 8.5/10

If you’re looking for an under-the-radar easy hike that packs a big punch then this is it! My 10-year-old and I did this hike after visiting Pigeon Point Lighthouse one afternoon in November. We got to the trailhead right around 4pm and hiked a mile to the top of the trail. The elevation gain is minimal and the views of the Pacific at golden hour were stunning, especially on a clear day! At the top, there’s a great viewpoint with redwood benches and a telescope. We looked for whales, found Pigeon Point Lighthouse in the distance and the moon too. By the time we got back to our car, it was almost dark. As we were pulling away, the sun was setting so we stopped to watch the sun sink below the horizon. Make sure to explore Pigeon Point Lighthouse, the beach & tidepools, and Whaler’s Overlook (just minutes away) – read about our entire afternoon here.

#1 – Big Rock Hole

Henry Cowell Redwoods State Park, Santa Cruz

Details

  • Distance: 5 miles loop (or about 1.5 miles roundtrip to the swimming hole)
  • Elevation: 800’
  • Our rating: Easy
  • No dogs
  • Parking: Free at the trailhead
  • Restrooms: Nowhere that I saw!
Swimming over to the rope swing at Big Rock Hole in Henry Cowell Redwoods State Park. Santa Cruz, California
Swimming over to the rope swing at Big Rock Hole in Henry Cowell Redwoods State Park

Our Rating: 8.66/10

This is a beautiful hike in Henry Cowell State Park with redwoods and river crossings. But that’s not why this hike came in tops – it was the beach and large swimming hole complete with a rope swing that we had to ourselves for a couple of hours on a hot summer day.

One thing my kids kept asking for this summer was a swimming hole. Honestly, it was hard to find one that was open and relatively close to us. As I read about this hike, it sounded really confusing and people talked about losing the trail. My kids were interested only in the swimming hole so we hiked straight there, hung out for a couple of hours, and then turned around and hiked back. While the entire hike is a 5-mile loop (Big Rock Hole -> Redwood Grove -> Ox Trail Path), we hiked maybe about a mile and a half of that. This is the Alltrails map – we hiked counterclockwise and the swimming hole was right along the San Lorenzo River ~ .75 miles from the start.

We brought a picnic lunch, blankets, and floaties and it was one of our best summer days. This was my 10-year-old’s favorite hike of the year and he was thrilled it came in at number 1 overall! We went early on a weekday in an effort to avoid crowds – we saw groups heading down the trail with floaties as we were hiking out. We will definitely head back here this summer when it’s warm again!

More Trails to Come!

This year we will continue to explore new hikes and revisit some favorites! I will plan to add more detailed posts on some of these 2020 favorite hikes and of course continue to post reviews & pictures for the new hikes we’re doing in 2021. My list of hikes to try seems to be growing daily, but I’m always looking for more! So tell me in the comments what hikes we should be sure to try!!

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