A Sleepy Hollow Summer: Where Your Thursday Nights, Saturday Mornings, and New Downtown Belong

Sleepy Hollow is 600 acres of wooded hills, and by design there is almost nothing inside it. No coffee shop, no restaurant, no gallery, no stage. That is the whole appeal, and it is also the reason living here well takes a little planning. The social infrastructure of this neighborhood is not on your street. It sits at three fixed points just outside it, and the summer of 2026 is the season all three finally line up.

The three anchors, and why that framing matters

Most guides to Orinda hand you a bulleted list of restaurants and trailheads and call it a day. That flattens something real about Sleepy Hollow. Ask a neighbor where they were last Thursday, and the answer is almost always one of three places: the club at the end of Sunnyside Lane, a fire road above Bear Creek, or a blanket on the grass at Orinda Community Park. Everything else in a summer week orbits those.

The value of naming them plainly is that once you see the pattern, you stop treating the neighborhood as a place with "nothing to do" and start treating it as a place with a very short, very good list.

Anchor one: Thursday Nights in the Heart of Orinda

The Thursday series returned June 4, 2026 and runs through October 1 at Orinda Community Park, 28 Orinda Way. Concerts are free, 6 to 8 p.m., with food trucks from Taste of the World Market. Once a month, a family movie replaces the concert and starts at dusk. Bring a blanket. That is the whole ask.

The 2026 lineup as published by the City of Orinda and The Orinda News:

Two things to note if you have lived here a while and stopped paying attention. First, Opera in the Park on July 23 is sponsored by the Rotary Club of Orinda and consistently draws the largest crowd of the season, so parking on Orinda Way fills by 5:30. Second, the movies now sit on alternate Thursdays rather than a separate Friday slot, so a single weeknight covers both.

Anchor two: the club at 1 Sunnyside Lane

The Sleepy Hollow Swim & Tennis Club is the reason a lot of people bought here, and it is worth understanding what it actually is. Founded in 1955 when a group of residents pooled money to reserve 45 acres as a green belt and recreation center, it is a member-owned nonprofit, not a country club subsidiary. That distinction shows up in the culture. Sunset Magazine described the pool as an "outdoor clubhouse and community gathering place" in a 1958 feature, and the description still fits.

The facility today includes an eight-lane competition pool from the club's first phase renovation, a separate activity pool with a waterslide and a shallow wading area for the youngest swimmers, and eleven tennis courts, several of which are now lined for pickleball. The Sleepy Hollow Legends swim team, for ages four to eighteen, competes in the Orinda-Moraga Pools Association league, and the swim program has been ranked among the top ten in Contra Costa County. If you have a four to six year old and were told the team is out of reach, the Mini Legend program is the bridge between learn-to-swim and full team.

For adult members, Masters Swim and the weekday fitness classes added in 2016 turn the pool into a legitimate morning workout before Highway 24 fills up. Court reservations run through Top Dog under the club's tennis director; the front desk at 925-254-1126 handles guest passes for out-of-town visitors, which is the workaround if your relatives are in for the weekend and want to swim.

Anchor three: the trailhead you already drive past

Briones Reservoir sits less than a mile north of the neighborhood, and the EBMUD trail system it plugs into covers over fifty miles across 27,000 acres of watershed land. This is not marketing copy. It is why a Saturday from Sleepy Hollow can start with a fire-road loop and end with a shower before ten.

A few specifics the maps do not always make obvious. The EBMUD lands require a trail permit, sold as an annual pass through the district, so plan ahead the first time. The Wagner Ranch EBMUD access ties into the American Discovery Trail, and the St. Stephen's pedestrian and bicycle trail, which starts at Bates Boulevard and Davis Drive and runs along the eastbound side of Highway 24 to St. Stephen's Drive, is the connector to Lafayette Reservoir if you want a longer flat loop without driving. The de Laveaga Trail from downtown links into the regional network for anyone who prefers to walk from the village rather than start at a trailhead.

For a first outing with visitors, the reservoir overlook loops are the right introduction. For a regular routine, most residents settle into one fire road they can do in under an hour before work.

What is actually new downtown

The reason to revisit downtown Orinda this summer is that two years of vacancies are ending at once.

The old Bank of America branch at 31 Orinda Way closed in March 2022 and has sat empty across from Community Park ever since. The site is being rebuilt as CreekHaus, a mixed food, coffee, and gathering space facing San Pablo Creek. City planning filings show the project grew from an original 2023 approval for an 8,810-square-foot two-level building to a revised 2025 proposal of 9,397 square feet with a 540-square-foot third story for storage and rooftop mechanical access. CreekHaus is being developed by Paymun, led by Orinda resident Ben Zarrin, and the project's own marketing tells residents that "Orinda Village is getting a new backyard this summer." An Equator Coffees cafe is confirmed as one of the tenants. Timelines on construction shift, but if the summer 2026 opening holds, this is the most visible change to the village in years.

At Theatre Square, the former Starbucks storefront next to the Orinda Theatre is becoming Sorso, a wine bar and small-plates concept from Daniele Carsano, a Turin native and Orinda resident of more than a decade whose other Bay Area projects include Montesacro in Walnut Creek and Casa Barotti in Berkeley. Sorso means "to sip," and Carsano has described the concept as a wine-forward bar with a light kitchen and a full cocktail program, aimed at giving Orinda a reason to stay in Orinda after the last show at the theatre. In his own words to the Bay Area Telegraph, he wanted a place "for great drinks, beautiful plates, and a community of people who love gathering around both."

Around those two anchors, the Square has quietly refilled. Shemroon Cafe, a Persian-inspired coffee shop, opened in November 2025 next door to the future Sorso space. Lamorinda Atelier, a contemporary art gallery, opened at the Square that same month. The Fourth Bore tap room and Serika, under relatively new ownership, are still holding down the food side, and the Boo Loo tiki lounge inside the theatre building gives you a pre-movie drink option that did not exist two summers ago.

Not everything is arriving. Morrison's Jewelers on Moraga Way closed in late 2025 after more than 102 years, with a handwritten sign in the window announcing that owners Dave and Chris are retiring. Worth noting the next time you are in the village and wonder where it went.

A Sleepy Hollow Saturday, in order

If you want a template a first-time host can hand a weekend guest without thinking:

1. Trail permit in hand, drive five minutes to the Briones overlook loop and be back before nine.
2. Coffee at Shemroon in Theatre Square, or Equator once CreekHaus opens.
3. Farmers' Market on Orinda Way, in front of the Community Park.
4. Lap swim or a court reservation at the club before the afternoon fills up.
5. Dinner from a food truck at Community Park on a Thursday, or small plates at Sorso once it opens, followed by whatever is on the marquee at the Orinda Theatre.

None of these steps require leaving Orinda. That is the point of the neighborhood, and this is the first summer in a while where the downtown half of the equation actually delivers on it.

The through line

Sleepy Hollow works because the quiet is protected and the interesting things sit a short drive from your driveway. The club has been the constant since 1955. The trails have been the constant since EBMUD set aside the watershed. The variable, for years, has been downtown, and 2026 is the year that variable finally moves in the right direction. If you moved here for the hills and stopped going to the village because there was no reason to, this is a good summer to change that habit.

When you are ready to talk about how this neighborhood fits your next move, or simply want a current read on what your home is worth in today's Sleepy Hollow market, Alexis Thompson is a call away. Get a free home valuation and let's start a conversation grounded in the streets you already know.