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Apple Picking in Oak Glen

Two young girls in plaid dresses picking apples in an orchard, surrounded by fallen apples on the ground.

Where Fall Finally Feels Like Fall Southern California

There’s something about apple picking that feels like stepping into a Nancy Meyers movie — cozy knits, crisp air, coffee in hand, and two toddlers in plaid who may or may not actually pick any apples. This year, we headed up to Oak Glen, a charming little mountain town in Southern California that feels worlds away from the suburbs below.

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First Stop: Snow Line Orchard

Come for the apple cider donuts, stay for the charm. Snow Line Orchard is a must for anyone visiting Oak Glen — it’s the perfect place to grab a warm donut and coffee before heading out for apple picking.

Alternatively, you can also visit Snow Line after you’re done apple picking. They have a winery, hard ciders, and live music! 

Next Stop: Los Rios Rancho

Apple picking, pumpkins, corn mazes, and a petting zoo — Los Rios Rancho has it all. With BBQ, live music, and plenty of space for toddlers to run around (and moms to sip cider), it’s the quintessential fall day.

ITINERARY

A woman wearing sunglasses holding a young girl with a white sweater and boots, in an orchard with green trees and mountains in the background, holding two apples.

Classic Apple-Picking Attire 

Think classic fall neutrals that photograph beautifully and can handle a bit of orchard mud. Quilted jackets, cozy knits, and timeless denim are always safe bets. For little ones, smocked dresses, quilted jackets, corduroy overall dresses paired with knee-high socks and Mary Janes strike that perfect balance between adorable and practical.

What We Wore

This time of year, I find myself yearning to look like I’ve stepped straight out of a Ralph Lauren catalogue — all tweed, tartan, and timeless charm. That’s hard to pull off in Southern California, where the temperatures seem determined to hover around 80 degrees until Christmas. But a trip to Oak Glen is the perfect excuse to ignore the thermostat and pretend I’m visiting Vermont in the fall. Because, let’s face it, dressing for fall in Southern California is really just and act of seasonal optimism. So I did my best to summon the cool, crisp fall weather in a navy quilted jacket, a cream sweater, jeans, and Hunter boots.

As for the girls, they looked like they’d wandered out of a children’s storybook — matching plaid dresses with sweet apple-button details, knee-high socks, and their little navy quilted jackets (which, if I’m being honest, never actually made it out of the car).

WHAT TO WEAR

SHOP THE LOOK

Navy blue quilted women's jacket with brown piping accents, four buttons, and a collar, displayed on a mannequin.
White embroidered sleeveless blouse with buttons and tie straps.
Cream-colored sweater with a dog design and the initials RLL embroidered on the front.
Pair of blue denim jeans with a straight-leg fit and a classic five-pocket design
A black Hunter rain boot with a buckle detail near the top and a red and white Hunter label at the top.
A navy blue quilted jacket with a black collar and tan buttons, partially unzipped to show an inside tag.
A children's dress with a red, navy, green, yellow, and white plaid pattern. The dress features short, ruffled sleeves and a row of red buttons down the front, with red scalloped trim along the button placket.
A single white athletic sock with a textured pattern.
Pair of children's brown leather shoes with decorative cutouts, scalloped edges, and ankle straps with buckles.

Apple picking in Southern California may be less about crisp air and more about strategic sweater choices, but it’s proof that fall is as much a feeling as it is a season. Days like this remind me that timeless style isn’t just about what you wear — it’s about the moments you create.

FINAL THOUGHTS

XOXO Love Ashley written in elegant cursive with a decorative accent for the word Ashley.