Classic movies, barn dancing, stargazing and a less-traveled hiking path. Find your passion, grab your date and hunt down the ice cream taco truck.

Hikes, food trucks, barn dances…mix it up lovergirl. (Monte Bello preserve by Kate Bradshaw. Other imagery via Yelp and Instagram.)

Date night is pressure: We love a regular hangout but if you can’t come up with something other than having drinks at the same bar you go to to watch the game, your potential partner would be better off hanging with work friends at a Bennigan’s (and the nearest one is in Sacramento for Chrissakes).

We’ve got ten fully fleshed out date ideas, all of them on the Peninsula and every single one of them guaranteed to leave you happier even if the relationship fails to achieve liftoff. They’re also all cheap or free and don’t require a ton of planning or effort because, well, we’re busy, too. Make the most of it.

More than 90 years old, the Stanford Theatre’s interior is a classy throwback to the golden age of cinema. (Photos by Charles Russo)

Catch classic movies in style at the Stanford Theatre in Palo Alto

Opened in 1925, this theater now runs with the sole purpose of showing classic films the way they were meant to be seen — on the big screen. A Peninsula landmark current screenings follow a “Hitchcock and Other Masters of Suspense” theme with some Frankenstein tributes mixed in. Whether or not it’s your instinct to try to impress a date with your extensive knowledge of classic movies (you don’t do this?), this place is a great excuse to dress up for a movie in a beautiful theater. We’re talking red velvet curtains and accent lighting. Screening times vary from matinees to 10 p.m. (though the norm is early evening). Have a stroll down University Avenue, grab some dinner nearby and enjoy a film on the big screen with your date beyond the latest superhero movie. Tickets are $7. Tip: make sure you bring cash, as the theater doesn’t take cards.

The Stanford Theatre// Wed. — Sat.; showtimes vary

221 University Avenue, Palo Alto, (650) 324–3700

Dosey-do on the hardwood, out at Pie Ranch in Pescadero. (Image via Pie Ranch website)

Farm, tour, eat and dance at Pie Ranch’s barn dance in Pescadero

Pie Ranch in Pescadero hosts a variety of community events, including food education and youth programs (see here for tips on visiting and other nearby coastside spots.) They also host a lively Barn Dance every third Saturday of the month. Dancing starts at 7 p.m. and goes for three hours, featuring live country-style music and, of course, dancing.

Better yet, make a day or an entire evening out of it. The dance is preceded by a 6 p.m. potluck dinner (bring a dish to share and enjoy some company, if you’re willing) and the potluck is preceded by a volunteer session from 1 to 4 p.m. followed by a farm tour (tour $12–20, volunteering is free).

“If you came to the volunteer workday, you’d start early, and you’ve got your hands in our soil, whether that be mulching or picking or planting,” Simone Albuquerque, the ranch’s program manager, says. “Working and taking the tour before the dance are a great starter for a conversation — perfect for a first or second date.” RSVPs to both the dance and the dinner are encouraged but not required (you won’t be turned away at the door if you forget).

The day will move quickly — “before you know it, it’s 9 p.m., and you’re under the stars with very little light pollution,” Albuquerque says. She passes on some other free advice: dress like you’re going to a farm, even though you’re going to dance.

Pie Ranch// Mon. — Fri. 12–5 p.m., Sat & Sun 10 a.m. — 5 p.m.

Barn Dance hours: every 3rd Saturday of the Month from 7 p.m. — 10 p.m.

2080 Cabrillo Highway, Pescadero, CA 94060, (650) 879–0995

Clockwise from top left: S’mores frozen custard from the Frozen Kuhsterd truck; noodles from SeoulBelly; a bounty of good from the ever-popular Jackrabbit; and a pint of root beer via the food truck scene at Devil’s Canyon’s Beer Fridays. (Photos via Off the Grid Instagram)

Chow and chill at Off the Grid in Menlo Park

Off the Grid started in San Francisco in 2010 as a market with a collection of food truck vendors and has since spread to 27 different cities in the Bay. Off the Grid Menlo Park happens every Wednesday, rain or shine, from 5 to 9 p.m. in the Caltrain station parking lot, which isn’t usually a space you associate with lively crowds but it works. It features a rotating cast of nine food trucks featuring cuisines from Asian to Russian to Mayan and different live music each week.

Our favorites: Cochinita’s vaporcitos (traditional Yucatan tamales steamed in banana leaves), the Waffle Roost’s ‘Spicy & I Know It’ fried chicken and waffle sandwich or a Reverse Reese’s (a fudge ice cream taco with peanut butter dip) from Rocko’s Ice Cream Tacos.

Off the Grid Menlo Park, every Wednesday 5–9 p.m., rain or shine

1120 Merrill St., Menlo Park

A colorful array of veggie heaven from Falafelle. (Photo via Falafelle Instagram)

Score falafel at the only Peninsula restaurant to make Yelp’s Top 100

Reasons to visit Falafelle in Belmont: it’s cozy (small, that is), pleases vegans, vegetarians and meat eaters alike and it’s #15 on Yelp’s Top 100 places to eat for 2018. It’s the only place on the Peninsula to have made the list (take that, Manresa!), which basically makes it a must-do even if you go home alone and lonely (it wasn’t the falafel’s fault). Take our advice: make a platter or customize your own falafel sandwich with the most colorful toppings you can get your hands on (beets, roasted red peppers and spicy tahini, to name a few). And try the Baklava.

Falafelle// Tues. — Sat., 11 a.m. — 3:30 p.m., 5:30 p.m. — 8:30 p.m.

1035 Ralston Ave, Belmont, CA

Looking skyward at the Foothill Observatory. (Image via the Foothill College website)

Stargaze (for free) at Foothill College Observatory on Fridays

Consider yourself the romantic type and interested in a date night spent (literally) under the stars? Foothill College Observatory hosts public evening viewings every clear Friday (you can get confirmations for viewings online here). What you’ll be looking at varies depending on the time of year and relevant astronomical goings-on. The observatory boasts two telescopes with impressive viewing capacity — one computer-controlled reflector and one hydrogen-alpha solar telescope, for those of you familiar with the subject (they also do daytime solar viewings). Evening viewings are free (!) and led by staff from 9 to 11 p.m. Just bring $3 for parking.

Foothill College Observatory public evening viewings: 9–11 p.m. every clear Friday.

Foothill College, 12345 El Monte Road, Los Altos Hills, CA (650) 949–7288

Fresh air and (lots of) open space in the Monte Bello Preserve. (Image via Yelp)
Vast views in the nearby Monte Bello Open Space Preserve. (Photo by Kate Bradshaw)

Do an easy hike to spectacular views at Monte Bello Open Space Preserve in Los Gatos

If you’re the outdoorsy type (or you’re trying to be) but you’re not in the mood to hike a 7-mile trail on a date, Monte Bello Open Space Preserve’s Stevens Creek Nature Trail might hit the spot. This 3-mile loop boasts a viewpoint where hikers can see Stevens Creek Canyon and a plethora of flora and fauna (speak that exact phrase on your date and watch the fireworks) in the spring and summer. Want to truly impress? Take your date to the preserve’s super-secret permit-only trailhead and pair it with a stop at Ridge Vineyards.

Monte Bello Open Space Preserve, Los Gatos, CA// Open daily, half an hour before sunrise to half an hour after sunset.

Midpeninsula Regional Open Space District: (650) 691–1200

A picturesque view of Filoli’s picture-perfect landscape. (Image via Filoli Instagram)

Stroll the gardens or take tea at Filoli in Woodside

Percy the Peacock making the rounds on the Filoli grounds. (Image via Filoli Instagram)

Filoli is a country house on a sprawling estate in Woodside that boasts amazing gardens set amid 670 acres and just celebrated its 100th anniversary.

General admission is $22 and includes access to the house and gardens, which flourish in spring and summer when flowers are in bloom. Take a romantic stroll then hit the Quail’s Nest Café in the estate’s visitor center. The menu is diverse and fairly priced. Feeling like showing your date an extra proper time? They also offer a tea for two for under $30.

Filoli Historic House and Garden// Tues. — Sun., 10 a.m. — 5 p.m. (last admission is at 4:30 p.m.)

Filoli Quail’s Nest Café// Tues. — Sun, 9:30 a.m. — 4:30 p.m.

86 Canada Road, Woodside, CA

(650) 364–8300

Go West! A short distance from the beach in Half Moon Bay, The Barn is a favorite among locals, tourists and surf seekers. (Photo by Sarah Klearman)
The Barn Burger is a Coastside favorite. (Image via The Barn’s Instagram)

Burgers and beach at The Barn in Half Moon Bay

The Barn in Half Moon Bay is legendary for its burgers (they also serve vegetarian options). Order at the counter, grab a table under some string lights and heat lamps on the outdoor patio and wait for your food with your date. Also notable on the menu: the pulled pork sandwich and the mac attack (fried macaroni and cheese). Best of all, the restaurant is a 10-minute drive from Half Moon Bay State Beach, so you can walk the trails on the cliffs above or relax and catch some sun on the sand below (maybe your digestive system’s best bet, if you took our advice and went for the fried mac ’n’ cheese). Heck, spend the entire day in HMB.

The Barn// Wed.– Sun. 11 a.m. — 9 p.m.

3068 Cabrillo Hwy N., Half Moon Bay (650) 560–8363

Here’s a date idea: try rustic and rowdy over posh and predictable, with Apple Jack’s in La Honda. (Image via Yelp)

Sip beer, stare at redwoods, appreciate AppleJack’s in La Honda.

Let us paint a picture for you. You’re wandering around the middle of the woods in La Honda with your date (we’ll explain later) and you’re absolutely desperate for a place to sit down and talk over some beers. One word: AppleJack’s.

This dive bar might be as offbeat as it gets and in the best way. It’s surrounded by land preserves and greenery and it’s got character, good beers on tap and the occasional dog hanging out on its front porch. Enjoy a few drinks with your date on the back patio (which is surrounded by redwoods) or have a beer at the dollar bill-covered bar (would you expect anything less?). It’s open until 2 a.m. Thursday through Sunday so take your time. Some advice: while there is a food menu, it’s short and mostly bar food — but we’re certainly okay with that, if you are.

AppleJack’s//8790 Hwy 84, La Honda, CA

Sun., Wed., 12–10 p.m.; Thurs. — Saturday, 12 p.m. — 2 a.m., (650) 747–0331

The airy outdoor environment at Backyard Brew. (Image via Yelp)

Learn salsa, drink coffee at Backyard Brew in Palo Alto

Have a coffee date with a twist (or, better put, a dip) and maybe without the caffeine (or go for it, we’re not judging ) at Backyard Brew’s Salsa Nights. Once a month through the summer — beginning April 27th and ending August 24th — the funky outdoor coffee shop off Palo Alto’s Cal Ave will host free salsa lessons at 6:30 p.m. followed by an open dance starting at 7:30 p.m.

“I allow people who are inspired to do whatever they feel like — I give people an outlet to do what they want to do,” says owner Ryan Khalil. The class will be led by salsa professional Taylor Kinney. Backyard Brew will be extending its normal business hours and serving its regular menu through the night. “We will be serving coffee but we won’t be behind the counter the entire time,” Khalil adds. “We’ll have some fun.” No matter if you can handle coffee late night or not, we can all agree on one thing: it’s a good window for some salsa under the stars with a dance partner.

Backyard Brew Salsa Nights// Call for info

444 California Ave., Palo Alto (650) 704–7785

Stay up to date with other coverage from The Six Fifty by subscribing to our weekly newsletter, featuring event listings, reviews and articles showcasing the best that the Peninsula has to offer. Sign up here!

More local eats from The Six Fifty:

Fruit Loop donuts and Double Doubles: Our gluttonous guide to late-night eats on the Peninsula

Cure your hangover and crush your hunger with our 15 favorite brunches on the Peninsula — 2018

The 650’s 3-minute guide to the Peninsula’s best ramen

Plant-based Peninsula: the Six Fifty’s guide to vegan & vegetarian eats around Silicon Valley

Sarah Klearman Profile Photo

Sarah Klearman

East coast transplant working her way through all things Peninsula. On Twitter @SarahKlearman

You May Also Like

Inside the San Carlos bakery crafting a gluten-free version of a San Francisco staple

Fired up: In search of Peninsula dining destinations offering fireside seats

The Six Fifty’s 2023 guide to Peninsula holiday performances, festivals and community gatherings

Culinary holiday happenings around Silicon Valley