Routes

Planner

Features

Updates

App

Login or Signup

Get the App

Login or Signup

Login or Signup

Routes
Hikes
United States
California
San Mateo County

Hillsborough

The best walks and hikes around Hillsborough

4.7

(92)

2,045

hikers

111

hikes

Hiking around Hillsborough offers a diverse landscape, characterized by pine flatwoods, riverine forests, and unique cypress swamps, with many trails made accessible by boardwalks. The region features the Hillsborough River, providing opportunities to hike alongside its banks and explore its natural features. While predominantly flat, areas like Occoneechee Mountain offer higher ground and varied terrain. These natural features create a rich and varied experience for outdoor enthusiasts.

Best hiking trails around Hillsborough

  • The most popular hiking route is Sugarloaf Mountain…

Last updated: May 1, 2026

26

hikers

#1.

Bayside Park to Robert E Woolley State Park Loop

4.28km

01:06

10m

20m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Navigate with device

Send to Phone

Save

Easy

3

hikers

9.67km

02:33

120m

40m

Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

Moderate
guide_signup
Let us show you the way with the komoot mobile app
With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures.

Sign up for free

Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

Moderate

5.0

(1)

9

hikers

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy
Sign up for free to see 107 more hikes around Hillsborough.

Get access to more routes and recommendations from other explorers.

Sign up for free

Already have an account?

Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

Start today with a free account

Your next adventure awaits.

Login or Signup

Popular around Hillsborough

Road Cycling Routes around Hillsborough

Running Trails around Hillsborough

MTB Trails around Hillsborough

Cycling around Hillsborough

Gravel biking around Hillsborough

Tips from the Community

Alex
June 25, 2025, Mariners Point

The Bay Trail wraps around Baywinds Park at Mariners Point. The views are great, and the trail is smooth and paved. Expect a bay breeze, especially windy in the afternoons.

1

0

San Andreas Lake is a hidden gem tucked into the hills of San Mateo County, just south of San Francisco. Originally a natural sag pond formed by the San Andreas Fault, it was transformed into a reservoir in the late 1800s and now serves as a vital water source for the region. The lake is off-limits for swimming or boating, but you can enjoy its peaceful beauty from the San Andreas Trail or the popular Sawyer Camp Trail, which runs along its eastern edge. It's a serene spot where you can walk or bike with sweeping views of the water and surrounding hills, all while standing right on one of the world’s most famous fault lines. Despite its proximity to urban life, San Andreas Lake offers a quiet, scenic escape steeped in natural and historical significance.

1

0

Located right on the water, this is a great place to walk, picnic, or workout on the outdoor gym equipment.

1

0

The San Francisco Bay Trail aims to encircle the entire bay across 500 miles of trails, paths, and roadways. As of now 2025 it is roughly 80% complete with over 350 miles open for use. This section along the water can be hiked in a loop, or connected to the wider trail to access other areas around the bay.

0

0

This small park punches well above its weight. There are great fishing, bird watching, and wildlife viewing opportunities. It's also located just south of SFO, so plane watchers can get their fill of watching the take-offs and landing.

0

0

A platform built in the marshes for observing flora and fauna

0

0

Watch out for fast-moving bikers on this lagoon-side trail, although walkers are welcome here too.

0

0

Will
December 7, 2023, Sugarloaf Mountain

Sugarloaf Mountain, sometimes more aptly called Sugarloaf Hill, is a simple and quick summit in the San Mateo area, offering some satisfying views of the greater San Francisco Bay Area. It is a great day hike destination if you are in the area.

0

0

Frequently Asked Questions

How many hiking trails are available in Hillsborough?

Hillsborough offers a wide variety of hiking experiences, with over 70 routes available for exploration. These range from easy strolls to more moderate paths, catering to different fitness levels.

What kind of landscapes can I expect to see while hiking in Hillsborough?

Hillsborough boasts diverse ecosystems, including pine flatwoods, lush riverine forests along the Hillsborough River, and unique cypress swamps, often made accessible by boardwalks. You can also find mixed hardwood forests, sawgrass marshes, and even sinkholes. While much of the terrain is flat, areas like Occoneechee Mountain offer higher ground and bluffs.

What do other hikers enjoy most about the trails in Hillsborough?

The trails in Hillsborough are highly rated by the komoot community, with an average score of 4.6 stars from over 80 reviews. Hikers often praise the varied terrain, from accessible paths along the bay to routes offering views from moderate elevations, and the opportunity to explore diverse natural features.

Are there any circular hiking routes in Hillsborough?

Yes, Hillsborough offers several circular hiking routes. For an easy option, consider the Sugarloaf Mountain loop from Laurelwood Park — San Mateo, which is 2.2 miles (3.5 km) long. Another popular choice is the Bayside Park loop — San Mateo, an easy 2.7 miles (4.3 km) path along the bay.

Can I find trails suitable for families with children in Hillsborough?

Absolutely. Many trails in Hillsborough are predominantly flat, making them suitable for families. The region's diverse conservation parks, like Lettuce Lake Conservation Park with its boardwalks through cypress domes, offer engaging and accessible experiences for all ages. Easy routes like the Bayside Park loop — San Mateo are also great for family outings.

Are there any dog-friendly hiking trails in Hillsborough?

Many of Hillsborough's outdoor spaces and conservation parks welcome dogs, though leash laws and specific park regulations may apply. It's always best to check the specific park or trail guidelines before heading out with your canine companion. Generally, trails through pine flatwoods and open areas are popular choices for dog walkers.

What natural landmarks or points of interest can I see along the trails?

Hillsborough's trails offer access to various natural landmarks. You can explore the Hillsborough River, which features rare Class II rapids, or discover unique cypress domes, such as those at Lettuce Lake Conservation Park. For higher ground, Occoneechee Mountain State Natural Area provides trails through bluffs. Notable highlights in the wider area include San Andreas Lake and viewpoints like Amazing Sunset Viewpoint.

Are there any trails with significant elevation gain in Hillsborough?

While Hillsborough County is predominantly flat, areas like Occoneechee Mountain State Natural Area offer trails with more noticeable elevation changes, leading to the highest point in the vicinity. For a route with moderate elevation gain, consider the Sugarloaf Mountain loop from Laurelwood Park — San Mateo, which includes over 125 meters of ascent.

Is parking available at the trailheads in Hillsborough?

Yes, most major conservation parks and trailheads in Hillsborough County offer designated parking facilities. Areas like Hillsborough River State Park, Flatwoods Conservation Park, and Lettuce Lake Conservation Park are well-equipped with parking for visitors. For specific routes, it's advisable to check the komoot tour details for parking information.

When is the best time of year to go hiking in Hillsborough?

Hillsborough offers pleasant hiking conditions for much of the year. The cooler, drier months from November to March are particularly popular, avoiding the peak heat and humidity of summer. This period also coincides with the annual Hillsborough Hiking Spree, encouraging exploration of the diverse trails.

Are there any urban hiking options in Hillsborough?

Yes, for an urban hiking experience, the Tampa Riverwalk provides a paved and accessible path along the Hillsborough River, offering scenic views and connecting to downtown areas. This allows for a different kind of stroll, blending nature with cityscapes.

Where can I find more information about Hillsborough's conservation lands and wilderness parks?

For comprehensive details on Hillsborough County's extensive conservation lands and wilderness parks, including information on specific areas like the Lower Hillsborough Wilderness Preserve, you can visit the official county website: hcfl.gov.

Most popular routes around Hillsborough

Easy hikes around Hillsborough

Most popular attractions around Hillsborough

Places to see

Store rating

Get inspired with the komoot mobile app

With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures.

or

Join komoot Now

Store rating

Explore more

Browse the best Hikes in other regions.

El Corte De Madera Creek Open Space PreserveTunitas Creek Open Space Preserve (Closed)Huddart County ParkPurisima Creek Redwoods Open Space PreservePacificaThornewood Open Space Preserve (Closed Area)El Corte De Madera Creek Open Space Preserve (Closed Area)Long Ridge Open Space Preserve (Closed Areas)Teague Hill Open Space PreserveButano State ParkPescadero Creek County ParkSkyline Ridge Open Space PreserveSkyline Ridge Open Space Preserve (Closed Area)Russian Ridge Open Space PreserveLa HondaLoma MarMemorial County ParkSan Pedro Valley County ParkHalf Moon BayLa Honda Creek Open Space PreserveLa Honda Creek Open Space Preserve (Closed Areas)BroadmoorBurleigh H. Murray Ranch State ParkWoodsideThornewood Open Space PreserveRussian Ridge Open Space Preserve (Closed Area)La Honda Creek Open Space Preserve (Permit Area)Moss BeachDaly CityCoal Creek Open Space PreservePortola Redwoods State ParkEast Palo AltoWindy Hill Open Space Preserve (Closed Areas)Baywood ParkColmaPurisima Creek Redwoods Open Space Preserve (Closed Area)San MateoMontaraRavenswood Open Space PreserveMenlo ParkRedwood CityFoster CityHighlandsPulgas Ridge Open Space PreserveAño Nuevo State ParkEmerald Lake HillsWunderlich County ParkWindy Hill Open Space PreservePortola ValleyBurlingameMiramontes Ridge Open Space Preserve (Closed)El GranadaPescaderoNorth Fair OaksBrisbaneLaderaSan BrunoPigeon Point County ParkAthertonBelmontMillbraeSouth San FranciscoSan Bruno Mountain State ParkWest Menlo ParkSan Carlos

Nearby adventure guides

Things to Do around Burlingame

background

Get ready to conquer new peaks

Sign up for Free

Explore
RoutesRoute plannerFeaturesHikesMTB TrailsRoad cycling routesBikepackingSitemap
Download the app
Follow Us on Socials

© komoot GmbH

Privacy Policy