Pioneer Saloon

This is a great place, they have karaōke with Sam Marshall every Tuesday.
He’s got quite a following and makes you feel like a star.
They have great bartenders and a great drink selection.
They just started having open mic on MOndays with Paul Brumbaugh, I hope it lasts.
I went to the last one and it was a hit.
The family running this place is really cool peeps.
The stage is great, great seats, the shows here are awesome.
This is nice gem of a place.

Our band played here, and did a good job, but then they stiffed us on payment. We have played over 300 shows at some 60 venues in over ten years and this is the only one that has ever done it.
In case they claim otherwise or think I am being unfair note I did write to the owners laying out our case and they never replied. So they had their opportunity to respond and chose not to do so.
We won’t be going back, and if you support live music please go somewhere else. Thanks!

If you want a fun place to hang out on weeknights the Pio as regulars call it is a great place to go for Karaōke. The DJ, Sam, makes karaōke a lot of fun. He also takes lots of photos and posts them on facebook if you want to see yourself signing. They only have one beer on tap (would be nice if they added more than just one) but overall I enjoy the place and it’s rustic feel, but I especially enjoy Sam’s karaōke. It’s a lot more fun than other karaōke places I’ve been to. They also have live music other nights of the week including sometimes Sam’s band, Marshall Law.

I’ve been known to have lofty expectations for a business that catches my eye. Whether it’s the signage or the shopping bag, if I like it I’ll try it. Being obsessed with California history and Westerns, I had such expectations for the Pioneer Saloon.
We were just close enough to Woodside last weekend so I decided it was time to cross it off my to-​do list. Cocktail (Manhattan) was generous pour and the bartender and locals were so friendly that I could have stayed for several more. Bar and the area has a very rich California history that the bartender was eager to share. Yay for me!
Beer snobs might do better with cocktails because Lagunitas and Sierra are as good as it gets, but that’s good enough for me. I understand that they have live music from time to time and I think it would be an amazing venue to hear some good olé’ rock music.
Will definitely return ANY and EVERY time I’m in the area!

There’s a whole one beer on tap here (Sierra Nevada), although there is quite a long bottled beer list, which runs the full gamut of what you’d expect from a dive bar (which it most definitely is), but none of these is worth of mention.
The place itself is pretty charming — there’s some fantastic windows, and lots of history — the bartender was super friendly, and had a clip book of newspaper clippings about the place (which has been there since 1882). There were even some bar snacks — tortilla chips (probably vegan) and popcorn (probably not).
I’m not really a fan of dive bars; I just can’t get past the bad beer, barfiles and TV sports, but for history in the region, you ought to take a look.

Went there after a holiday party for work with a few co-​workers. We weren’t expecting much. There are two options to enter (front & back). They choose to set up their cover-​charge handler in the middle of the bar not at either door, which makes zero sense. Okay, fine, we pay since the band seemed good. Got a round of drinks and the females got up to dance. Had to help a friend fend off a dude a few times, typical though so no biggie. Sat back down with our group and the guy that needed fending off turns out is a regular (I’ll be nice and omit his name). He comes back in and can barely stand up, I make a comment about being drunk to my co-​workers and he blows a gasket. Starts trying to get physical with the guys in our group and making rude and lewd comments to the women in the group. Long and short of it he was a drunk douchebag who needed to be tossed out on his ass so other, respectable, paying, non-​drunk, non-douche’y patrons could enjoy their time. The «bartender» (using the word ever so lightly) comes over and nonchalantly tells said douchebag «leave» and that’s it. Meanwhile this guy is still going off and trying to get physical and the bartender just stands there. If there is one thing I dislike most, it’s someone who won’t do their job. If the place can’t afford a bouncer/​security than the bartender takes on that role for the safety of the patrons. Said bartender was not happy with me when I called him out for his lack of care in dealing with someone he clearly knows. I guess in this place you can be a douchebag and threatening to others if you are the known barfly. He didn’t take kindly to me asking that he put in a little more effort in getting this known asswipe out of the building cause he threatened to call the sherff on me. This was where I laughed out loud for a few reasons, 1. who calls the «sheriff», most people just say cops and 2. because I guess the sheriff has nothing better to do on a Friday than to be called to a bar because there is a lady who is merely telling the bartender, in a non threatening manner, that he –for the lack of a better word — being a p$%%y and putting others in jeopardy because of it.
Pros: good band, seemed clean, drinks were ok
Cons: bartender, bartender, bartender

When you advertise that your hours are until 10 PM, don’t turn people away saying things are closed at 8:56 PM. Not rocket science.

Def an old saloon/​dive but super fun, great drinks & reasonable prices. Live music is OK, generally a small cover but the crowd gets super into it!

Awesome place with a mixed crowd and live music all the time. Something about walking into a place that you know was around in the gold rush.

first time going to The Pioneer Saloon last night with a couple buddies. 12 hours later and I still have ringing in my ears from the blues band that played last night. And not to mention I think I saw Angelina Jolie & Julia Roberts sitting at the bar. We’ll be back for sure.

I used to work in Woodside and stupidly drove past the Pioneer many times… didn’t stop in until last Friday night and had so much fun.
I’m not often in this neck o’the woods but when I am I hope someone with as much countrified goodness as the Legendary T.B. Slick Revue is playing, and that the patrons and bartender are every bit as friendly as they were last week.
Certainly well maintained and super clean for a «dive bar» so I wouldn’t call it that at all, but if you like hellbilly music and dancing this is the place for you. I’ll be back!

been there once. I would go again if I were forced to… good place to go if you want to ‘slum’ it.

this is an absolutely excellent venue for local entertainment. It’s a friendly, inexpensive bar with an older, but fun crowd. The live music is truly something special with many talented musicians donating their time. Especially on Sundays, the bartender is great and the service is excellent. I live in Redwood City and would return frequently.

Absolutely wonderful atmosphere and the drinks are strong! My girlfriends and I love to come here on Thursdays and witness the top live bands play here. Bartenders always know how to make some special girlie drink and keep us chatty! Perfect place for the mysterious aura of Woodside. It feels like you are back in the old days when booze was pouring and the gentlemen opened doors for ladies! If you want to experience a warm, welcoming atmosphere and be surrounded by the woods, definitely need to come here! Special thanks to Bree!

Who would EVER think that such a mecca of talent resides in such a back woods location? The Sunday Jam draws some of the best musical talent anywhere… Seriously…Like festival headliners! Chris Cain, Kenny Neal, Daniel Castro and many others. Every sunday the placed is jammed to the rafters with people who come out to enjoy the reasonable drinks generously pounred by every’s favorite Bar Tender– Angela. And «Running with Scissors» is the house band.
People ride up on horses and tether then outside… one of these dropped his fingerprinted Tesla key chain– so methinks these are not run of the mill cowboys!
THis place is a casual place. Jeans, shorts, tennis shoes and boots abound. Not a place to get food (they don’t even serve it) I suggest ear plugs if you want to sit inside– the place is SMALL and the music is BIG… they even offer a cup full of plugs on most Sundays– but bringing your own can never hurt.
People are nice and friendly, laid back and easy to get along with. What’s not to like. Parking is plentiful and free… and there is no cover charge for the Jam.
FIVE STARS!

Depends on the bartender.
If you get one of the aged and miserable bartenders, you’re better off driving into Redwood City, San Carlos, Palo Alto, etc. but if you’re looking for a dive bar in Woodside it’s pretty much your only choice.
Also depends on cleanliness whether you should wear some beater shoes or not, because the floors get sticky. Sometimes there’s live music. I live two minutes away but usually take the extra twenty minutes to drive somewhere cleaner and more enjoyable.
Perhaps with a cleaning crew and mostly new staff that place would be great.

After reading the other reviews, I had to chime in as most of them were a few years old. I am over 30 but under 50 and I enjoy the crowd, drinks, décor, & atmosphere. The other review about the patrons being rock stars to cowboys was dead on. I don’t fit in with most of the locals, but I don’t feel uncomfortable either. Bartenders fun & smiling, crowd following suit. Sunday jam is great to sit back & watch as I ALWAYS bring ear plugs. (It can get ridiculously loud but the there are ear plugs at the bar.) Last weekend a pizza truck was there & made pretty good pies.
Ask Angela for a bloody Mary & you WILL NOT be disappointed!

Why 5 Stars?
This place is one of a kind.
I’ve played here maybe 20 times over the years with various bands, and its always a great time. even if i just stop in for a beer to pass on traffic, the patrons are always very cool, social, accommodating (offer you a seat), and all around the experience is good. Management is doing something right, and the bartenders have always been spot on.

Feels like I just stepped back in time walking around Whiskey Hill. The bar is really small, I was expecting a bigger space. My guess is from where the bar stools are, it is about 10ft to the wall? The length is about 30ft? This is with a small stage set up there.
We went on open mic night, so it wasn’t all that packed. Everything about this place has charm to it. The ceiling has metal square coverings. Found out that is is 126 years old. So much history. I just couldn’t stop thinking about what it must have been like in the old days here? Probably way more wild. Yee Haw.

Palo Alto Pub Crawl Stop #7. (Actually Woodside stop #1). One of my buddies absolutely insisted we go to the Pioneer at the end of the night. A few of us had never been there (including myself), which sealed the deal for everybody else. So after fortifying ourselves with some pizza, we grabbed a cab to this Woodside institution.
Considering the size of the building, I was expecting a cavernous, barn-​like interior with a big dance floor and spacious stage. I couldn’t have been more wrong. The place is TINY inside, with a short stage practically crowding up against the patrons in the small bar area. The music from the 3-​piece rockabilly band wasn’t too good that night, and the room was claustrophobic, so after grabbing a round of Sierras we shuffled back to the other small room, which is half-​filled by a pool table. At least no one was playing pool, so we had the table to ourselves. We proceeded to play a few games and hang by the faux fireplace.
Based on my single visit, I can’t say I’m a huge fan of the Pioneer. But it has a certain appeal. This is a real dive, not a place just aspiring to be a dive, nor a place just *furnished* like a dive. It’s the real deal, and after midnight on a Friday night the crowd consisted of locals, bikers, ranchers, and serious barflies. There was even a young pool shark, who challenged my friend ML to a game at the end of the night… and was scary-​good. My friend put up a valiant effort but lost the game. Per previous agreement, his payout was to buy everyone in the place a round. Since it was the razor’s edge of last call, however, most people were already good-​to-​go, and my friend got off cheap.
Pub crawl over, it was time to catch a cab and make our way homewards.