The Ennisbrook Trail meanders through some of the most enchanting oak forests in the Montecito area. 
A white picket fence and building mark the beginning of the Ennisbrook Trail. 
This historic stone bridge tha once led to the Rancho San Leandro adobe. 
At the beginning of the walk you are immediately immersed in a canopy of oak trees. 
Ennisbrook is a wonderful place to walk your dog. 
This trail junction is where the upper loop trail begins. 
There is a eucalyptus forest on a side trail along the upper loop of the Ennisbrook Trail in Montecito. 
Main trail along the upper part of the Ennisbrook Preserve. 
Not everyone is on foot. Be on the lookout for equestrians on the Ennisbrook Trail.
The walk begins at the edge of a picturesque white picket fence, enhancing the sense that you are about to enter a private preserve.
In actuality the enchanting forest beyond the fence is a 44-acre open space that meanders along San Ysidro Creek for three-fourths of a mile, once part of a much larger Mexican land grant.
Within yards you cross over the first of two stone bridges, beautifully constructed of large hand-hewn blocks of sandstone quarried from the nearby mountains, that led to Rancho San Leandro 150 years ago, a magnificent estate constructed in the 1840s by a retired Presidio soldier by the name of Nemecio Dominguez.
The Ennisbrook Trail is dominated by forests of California live oak, many which may have been in place when the land grant was first created.
The walk is almost perfectly level as it winds its way through the woods and over the stone bridges and along the creek, making the hike perfect for families, those who enjoy a quiet stroll or like me, a spot away from other more crowded trails for a walk with our English bulldog, Myrtle.
At the upper end of the walk, the trail makes a half-mile loop around what may be the most enchanting oak groves anywhere in the area, providing a glimpse of why the Presidio soldiers who settled here such as Dominquez called the area Montecito, which is Spanish for “little forest” or “little woods.”
Ennisbrook is also known for its nearby neighbor, Oprah Winfrey. You can glimpse a bit of her 42-acre estate, named “The Promised Land” in honor of Martin Luther King, from the upper part of the loop trail, though most of it, including the main house, is hidden from view by the oaks.
A caution — while the ground cover beneath the oak trees is quite attractive, it also contains copious amounts of poison oak. Staying on the trail is a must and a good reason to keep your dog on a leash.
Getting There
From Santa Barbara, drive southbound on Highway 101 to the San Ysidro exit in Montecito. Turn left, cross Highway 101 and then turn right onto North Jameson, the frontage road. Follow North Jameson .3 miles to the stop sign at Hixon Road. Turn left and continue north to San Leandro Lane. Turn right on San Leandro and go east .25 miles to the trailhead. You can’t miss the white picket fence where the hike begins.
Hike Details
Length: 1.75 miles for the entire loop hike. It is 3 miles if you loop back through the Ennisbrook estates complex to Sheffield Road and then follow the hiking trail back along San Leandro Road to your car.
Gain: 160-foot gain from the trailhead to the top of the main loop; Add a 120-foot gain if you loop back though the Ennisbrook estates.
Difficulty: Easy
Restrictions: The Ennisbrook estates complex is privately owned. An easement along the south side of Jelinda Lane allows public access through to Sheffield Drive. Please do not wander off onto other parts of the complex.
Canines: The trail is designated for dogs to be on leash.
Resource: Download the geo-referenced PDF map of the Ennisbrook trails for use when you go for a hike there.
Historical Notes
Ownership of the property dates back to the 1840s when the retired Presidio soldier, Nemecio Dominguez, was granted a half square mile of Pueblo lands in the Montecito Valley that he named Rancho San Leandro.
A quarter-mile onto the property, and just a few yards east of San Ysidro Creek, he constructed the main house, known then as the Dominquez Adobe.
Over the next century the estate would be become the site of a farming operation, a horse racing track, several polo fields and would eventually become known as a center for polo events, both locally and nationally.
After the Great Depression and start of World War II combined to reduce interest in polo, the rich green polo fields turned to weeds and for many years, little was done to care for the property.
Eventually the property was purchased in 1986 by two developers who were able to get Santa Barbara County approval for construction of 63 homes on the former site of Rancho San Leandro with the proviso that they deed a 44-acre chunk of the property for the site of what would become Montecito’s first nature preserve.
On the Trail
No matter how many times I visit Ennisbrook, I always find myself slowing down, listening more and taking my time.
0.0. Crossing past the white picket fence, the trail immediately becomes immersed in a canopy of oak trees, thick enough to filter the light and dampen outside sound. The trail crosses the first of two stone bridges and meanders along San Ysidro Creek.
.25 miles. Trail approaches the Ennisbrook estates. Jelinda Drive leads directly to the east to Sheffield Drive. An easement along the right side of Jelinda provides public access. Trail continues north paralleling Ennisbrook Drive for 300 yards.
.42 miles. Ennisbrook Drive turns east. The original Rancho San Leandro adobe is across the road but hidden by oak trees and other vegetation. Trail continues north along the creek and crosses San Ysidro Creek at the second stone bridge.
.5 miles. After crossing the creek the trail heads due north. The Oprah Winfrey estate is to the west beyond a chain link fence but is mostly hidden from view. Beware any attempts to head off the trail to get a closer look at her estate. The poison oak is quite thick along this part of the trail.
.65 miles. A trail intersection marks the beginning of the upper loop. Continue north to follow the loop clockwise or turn right, cross a tributary of the creek and follow the loop counter-clockwise.
.8 miles. Hiking counter-clockwise (my preference), the trail meanders through lush forest to a second intersection. The main loop trail continues to the left. The right fork dead ends on the other side of San Ysidro Creek in a massive grove of tall eucalyptus trees that is worth checking out.
.95 miles. Trail comes to East Valley Lane, a small neighborhood road that leads north to East Valley Road. The trail curves to the left and begins to head back downhill to your starting point.
1.1 miles. East Valley Lane ends at a cul-de-sac. Trail widens and continues downhill through the oak forest.
1.2 miles. Trail comes to the intersection marking the lower loop trail.
1.5 miles. Trail re-crosses the creek and parallels Ennisbrook Drive. To extend your hike, head east along the side of Jelinda Drive.
1.75 miles. White picket fence marks the end of the walk.
Extend the Hike
As mentioned above, it is possible to extend your hike by following Jelinda Drive east along a public easement and loop back via Sheffield Drive and San Leandro. This will add about 1.5 miles to your hike and has the added bonus of providing an opportunity to check out some of the massive homes within the Ennisbrook complex.
There are a few tricky sections to getting to Sheffield but if you use the map of the Ennisbrook Trail network you shouldn’t have any problem finding your way.
0.0. Head right onto Jelinda Drive and follow it for .7 miles as it rises gently, climbs over a small knoll and drops downhill towards Sheffield Drive. While the actual trail easement along Jelinda should be off the pavement, over the years most of the homeowners have encroached on it, thus requiring hikers to walk on the road. But no worries. The road is extremely wide and the traffic fairly sparse.
.75 miles. Look for an MTF trail sign on the right. The sign marks the point where you’ll turn right off Jelinda and onto a narrow dirt pathway. That will take you between two of the estates and then down to Gould Lane.
.9 miles. The trail intersects Gould Lane. Turn right on Gould Lane go just under 100 yards and look for another MTF trail sign on the east side of the road. It may be hidden a bit by the vegetation but it marks a short section of trail that leads down to Sheffield.
1.0 mile. Sheffield to San Leandro — follow the trail along the right side of Sheffield for just over 100 yards until you can see the San Leandro intersection below you. The trail curves to the right and heads west between a third set of homes then drops down to San Leandro.
1.2 miles. Continue along the trail as it parallels San Leandro Lane for just over a half mile to the trailhead.
1.75 miles. End of the hike!
— Noozhawk outdoors writer Ray Ford has been hiking, backpacking and bicycling in the Santa Barbara area since the 1970s. He is a longtime local outdoors columnist, author and photographer. His previous work can be seen at his website, Santa Barbara Outdoors. E-mail him at rford@noozhawk.com. Follow him on Twitter @riveray. The opinions expressed are his own.
