Our favorite local dining attractions:

Mostly staying West of 280, all available via country roads). 

Alpine Inn: https://www.alpineinnpv.com/

At the bottom of the hill.

Longtime roadhouse and beer garden, now under new ownership and thriving. Can be busy (and, can be easier if you walk; at the lower end of Golden Oak, at the upper end of the road barrier, you'll find a path that takes you down and avoids having to walk on the street on that tricky curve). Busy days mean a 90-minute maximum; all ordering is via your mobile device, and there is a great menu, wine list, and full bar. Played a part in the origin of the Internet: https://www.theguardian.com/technology/2016/jul/15/how-the-internet-was-invented-1976-arpa-kahn-cerf

Amigo's Mexican Cantina

In Ladera Shopping Center. 

Locally owned, best carnitas in town, and the owner, Don Pilar, is also a renowned Tequila distiller.  https://www.donpilar.com/

Buck's of Woodside: http://www.buckswoodside.com/

On Woodside Road (can be reached by scenic back roads). Popular and famous for decades; at one time the Elaine's of Silicon Valley. Inside is a kid's paradise -- the owner's collection of memorabilia. 

Flea Street Cafe: https://www.cooleatz.com/
Down Alpine Road (which turns into Alameda De Las Pulgas (Avenue of the Fleas).

Founded by Jessie Cool decades ago -- the Alice Waters of the Peninsula. Frequently voted the best in dining. 

Koma Sushi Portola Valley:https://komasushiportolavalley.com/

In Ladera Shopping Center.

First rate Sushi restaurant with indoor and outdoor dining, in the Ladera Shopping Center. 

Madera (at the Rosewood) http://www.maderasandhill.com/

In the nearby Rosewood Hotel, (can be reached by back roads, or, the first exit North of Alpine off 280).

A lively bar and a generous outdoor area. Fine dining, highly rated, and a family favorite. 

Parkside Grill: https://parksidegrille.com/

Alpine road, right, to Portola Road, right.

Set in the redwoods nearby along Portola Road, a local favorite with beautiful outdoor dining and a diverse menu, great wine list. 

Village Bakery: https://www.tvbwoodside.com/

Sister to the Village Bakery, and a local favorite, with outdoor seating including a secluded patio. A classy bakery restaurant combo that is highly recommended. On Woodside Road. Can be reached by back roads.

Village Pub: https://www.thevillagepub.net/

Very fine dining;,prix-fix multi-course dining with caviar choices, and a treat. Yet, there is a pub menu option, so you can still get a couple of great cheeseburgers and a bottle of Caymus Cabernet for under $650.

($600 for the Caymus).  Off Woodside Road.