The Ultimate Guide to Hiking the San Francisco Crosstown Trail With Your Team

Everything You Need to Know About This Handstand-Approved Adventure

We know a great group activity when we see (or create!) one, so we're excited to share our newest favorites with the Handstand community: The San Francisco Crosstown Trail. It is the best and most beautiful hike in the city, and an awesome team-building activity.

When we did the hike, we were all grinning, and although we were a little sore, we felt completely energized. It's a wonderful SF adventure that is quickly becoming a common bucket list item, and whether you enjoy it with coworkers or friends, we know you'll be happy you did it!

We break down everything you need to know to have a great day – highlights, section details, bathroom stops, beverage stops, and more.

10 Quick FAQs about the San Francisco Crosstown Trail Route

1. When was the route established? 2019.
2. How many miles is the Crosstown Trail? 17 miles! You can break this distance up into segments.
3. How long does it take to hike the Crosstown Trail? Allow 6-8 hours, depending on the number of stops and their duration. We stopped for a two-hour lunch, so it took our group 8 hours total.
4. What is the trail type? It is a combination of asphalt trails, dirt trails, wooden planks, and city streets.
5. Is the Crosstown Trail hard? We rate this as an overall Moderate hike due to the distance. Sections range from Easy to Easy-Moderate because of stairs and elevation gain.
6. Where does the hike start and end? The trail cuts diagonally across the city, starting at Candlestick Point and finishing at Sutro Baths.
7. How should I navigate? You can follow this AllTrails route.
8. What should I bring? Bring clothing layers, water, snacks, and sunscreen – even if it's foggy!
9. What makes the Crosstown Trail unique? This hike is almost entirely made up of parks and nature areas within the city. You also go through residential areas you wouldn't necessarily visit, and see stunning views.
10. Why is the Crosstown Trail a good team-building activity? You're outside, moving your bodies, exploring new parts of the city, and hanging out in a relaxed environment. Plus, you ultimately have a shared group accomplishment you can be proud of. Sounds cool, right??

What to Expect on the Crosstown Trail Hike

It's a moderately strenuous trek, featuring several staircases and noticeable elevation changes along the route. The total elevation is 2,000 feet, and most of the ascent is very gradual. As you hike, you pass through neighborhoods, city parks, beautiful nature reserves, and stunning views. If you're ever tired, just remember: elevation = views! Here is a look at the full 17-mile route in green.

Why It’s Handstand-Approved

The San Francisco Crosstown Trail is the full package—city parks, nature trails, local cafes, and quirky dive bars all in one experience. Handstand was born in SF, and we love celebrating the city through movement, play, and shared discovery. It's even better when the experience supports local community businesses along the way.

The Crosstown Trail hike feels like a free-form scavenger hunt chock-full of discoveries for locals and tourists alike. While the full 17 miles is an epic accomplishment and completely worth it, you can always choose a chunk to bite off with your group to make the adventure more manageable and accessible for folks.

San Francisco Crosstown Trail Tips & Segment Highlights

Alright. Let's be clear. Our esteemed recommendation is to do the full route. It does require a full day. It's also 10x more enjoyable on a sunny day to fully appreciate the stunning views above the Bay, Ocean Beach, and Lands End. So aim for that!

Where and When to Start the Crosstown Trail Route

To start, split an Uber out to Candlestick Point to avoid having to return for your car. Depending on the season and amount of daylight hours you have, try to kick it off around 8 or 9 AM and finish at 6 PM. That timeline includes a long lunch break (and a beer or two).

Keep reading for details about each segment of the route!

A Breakdown of the Crosstown Trail Segments

When thinking about the Crosstown Trail, you can break it down into 4–5 mini-adventures, which we explain below. Within each segment, we recommend cafés, must-see stops, and share available restroom areas.

If you want to test out the trail before making the entire trek, you can choose one of the sections! No matter how you go about it, the Crosstown Trail is a great team-building activity for SF-based teams, and a fun experience with friends.

To navigate, you can download AllTrails and follow this route or use these Pease Press maps!

Segment 1: Candlestick Point → McLaren Park

Distance: About 3 miles

Difficulty: Easy. Slight elevation to McLaren Park.

This section takes you along the water, through Visitacion Valley, and into the city's third-largest park, McLaren Park. There are glimpses of the Bay and small cafés alongside quaint community gardens.

Tip: Bring a hat, as there is minimal shade on this section. Also, stop at Mission Blue Café (Visitacion Valley) for coffee and local artists' goods!

Hidden gem: Candlestick Point is a State Park Recreation Area. This is where Candlestick Park (#RIP) used to be!

🚻 Restrooms are available at cafés in Visitacion Valley. Other than this area, there are no public restrooms until Glen Canyon Park.

Segment 2: Glen Park → Glen Canyon Park → Laguna Honda Trail

Distance: About 5 miles.

Difficulty: Easy-Moderate. A few stairs along the route and several downhill inclines behind Sutro Tower.

From McLaren, the trail heads into one of the most immersive nature zones of the day. During this section, you'll enjoy a surprising sense of being surrounded by nature right in the middle of the city. Walk through Glen Park's neighborhood hub, meander along the canyon, and continue through beautiful eucalyptus trees on the backside of Twin Peaks.

• Hidden spot: Take a detour to Sunnyside Conservatory for secret garden vibes.
• Local business: If you're looking for food and drink, pop into some Glen Park spots. You can try Canyon Market, a cute local grocery store, Bello Café for coffee, or Higher Grounds Coffee House, which specializes in crepes.
• Local gem: Glen Canyon Park. There are a bunch of trees, flowers, and plants to keep an eye out for!
  • Willow trees
  • Horsetails
  • Seep monkey flower
  • Red columbine
  • California poppy
  • Blue-eyed grass
  • Checkerbloom
  • Mule’s ears

🚻 Restrooms are located at Glen Park businesses or Glen Park Recreation Center. The rest of the section (and the rest of the walk until after the tiled stairs) is residential.

Section 3: Golden Gate Heights Park → Grandview Park → Tiled Stairways

Distance: About 3 miles.

Difficulty: Easy-Moderate. Several sets of stairs.

Enter: Stairs. But hey! Stairs = views. And trust us, they are worth it. You get some wide-open skyline reveals on this section that we would rate as the best views of the day.

• Must-see spot: Don’t miss the Grandview views, the 16th Avenue Tiled Steps, and the Hidden Garden Steps. Iconic photo ops.
• Local business highlight: When you get down into the Inner Sunset, you can take a pit stop at the Chug Pub for tacos and a libation of choice. Cheers!

🚻❌ There are limited bathroom options on this section until you hit the Sunset!

Section 4: Blue Heron Lake → Rose Garden → Park Presidio Boulevard → The Presidio

Distance: About 3.5 miles.

Difficulty: Easy.

Time for some Golden Gate Park action! In Section 4, you'll get the chance to appreciate all that Golden Gate Park has to offer in even just a tiny section of the park: wide trails, paddle boats, gorgeous roses, redwoods, and endless picnic options. If you are doing just this section and want a pit stop, you can rent paddle boats at Blue Heron Boathouse.

• Must-see spot: If you're hiking the trail mid-May through June, you're in luck. The roses in the Golden Gate Park Rose Garden will be in bloom! Take a few extra minutes to stop and smell the roses.

🚻 There are bathrooms towards the middle of the park by Blue Heron Lake.

Section 5: Presidio → Sea Cliff → Lands End → Sutro Baths

Distance: About 3.5 miles.

Difficulty: Easy-Moderate. There are several sets of stairs and some steeper sections on the Lands End trail.

This section will make you feel extremely grateful for and in awe of San Francisco. The stroll through the Presidio dunes was a fan-favorite chunk of the hike.

Overall, this section is marked by crashing surf, wind-whipped cypress trees, and, if you time it right, a Sutro Baths sunset. We recommend reading the signs at the top of the Sutro Baths stairs by the parking lot to learn some history about the bathhouse and the fire that consumed it. If you want a break on this route, Baker Beach is a great place to stop and take in the views of the Golden Gate!

Nearby food gem: Lou’s Café (Outer Richmond). Stop at Lou's for yummy sandwiches.

Victory view: End your journey with ocean air and a group or team selfie.

🚻 There are bathrooms at the start of the Presidio, located by the pond and basketball courts. There are also bathrooms at Sutro Baths, but they are sometimes closed in the evenings.

Tips for a Trail-Based Team Outing

🛑 Add extra stops. Make up some fun team challenges at different checkpoints, or do blind taste tests from local shops!

🎭 Build a theme. Wear hilarious costumes along your route for the ultimate bonding experience.

🧭 Encourage detours. That's part of the fun. You're already exploring, but explore a little more off the trail.

⛓️‍💥 Break it up. Pick a 3–5 mile segment for a half-day outing.

Who is the Crosstown Trail For?

Honestly, we think the Crosstown Trail is a San Francisco experience everyone should get a taste of.

It's perfect for folks wanting to see a new side of the city, and for corporate teams who want to bond outside.

Now, Get Out There.

Go have fun! Build connections with your group throughout the day and make sure to celebrate your shared accomplishment at the end!

For more San Francisco team-building adventures, check out our list of the 10 best team-building activities, or schedule a Handstand scavenger hunt!