You had me at live music Came to support David Hobbes & really enjoyed the space. Older crowd (37) but I fit in well too Single bartender holding it down. Live music most Thu-sun it seems. Support an artist trying to sing! read more

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Best bar in Wooodside. Small but pretty friendly. Mainly locals. Some good history. Live music.

Venue has been very accommodating and service has been very good. They consistently have live music in a intimate historic venue.

What I like about Pioneer : Good music , rockin drinks . Always a good time in Woodside when we eat at Bucks then mosey on over to the Pio for drinks and some dancing. Sam Marshall and Dutch Uncle are two of our favorites. Angel makes incredible mixed drinks and Mocktails as well. read more

Pioneer Saloon - Handsome greeter - Dive Bars Near Me - Woodside, California

Some locals recommended this place since it had music and stayed open later then 8pm on a Friday. And we were warned that the drinks weren't good. And that part was true. It was definitely for an older older crowd. And they charged us cover charge but everyone else went in free. Idk maybe Bcse we weren't locals. Other than that it seemed like a chill place to go to if you're older and don't like to drink mixed drinks. The service was nice though. Very nice. read more

The band was good I would give them 5 stars. The bartender sucked. Second glass of wine he barely gave me half a pour and did not give me a clean glass. My husband left him a tip but he really shouldn't have! read more

Not sure what keeps this place going. Drinks are watered down. People are not friendly. Must just be for locals. I would skip it.

Went here with my girlfriend after visiting Filoli nearby. Seems like a nice spot. Oddly, this town is mostly a bedroom community for Silicon Valley VCs. We kept trying to guess which bar patrons were VCs. read more

I frequented this place years ago when I was working at a motorcycle shop and always enjoyed myself. I went there to watch a friend whom performed and was able to learn LINE DANCING, which was a real kicker. Enjoyment is the meaning of this delightful place. Thank you read more

First time going there tonight and I was very pleased! Great atmosphere and awesome live music, will definitely be returning.

You're pretty much guaranteed a fun night at the Pioneer! Before we had kids, we'd to come to the Pioneer all the time with Woodside friends - at least a couple times a month. There's always a live band (usually a $5 cover though for the band - ATM right outside if you forget to bring cash) and great people-watching of a crowd of all ages. The drinks are reasonably priced and they even have decent (though not great) red wine options. We don't make it out nearly as much now but we've spent the last two New Years Eve's at the Pioneer and had a great time with friends. The Pioneer will likely continue to be our New Years Eve (and other bar nights) tradition! read more

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. read more

This place is OLD SCHOOL! I came out of curiosity last night after work and i must say i loved it! it's divey, but they had a live band and a dance floor. You definitely need to get a ride to and fro cuz you'll have a fun time and i don't recommend you attempt driving home afterwards. folks there are not pretentious. just laid back and real friendly! if you wanna get away from the inner city and just let loose to drink, socialize, and dance you'll love this place! Drinks are not super expensive either. Cheers! read more

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, decor, & 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! read more

This is a great place , they have karaoke 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. read more

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. read more

What a treasure! A day spent at great basin, on the way home to east bay off the 35, came through woodland town and found the Pioneer Saloon!! What a historic place and AWESOME people we meet for just a quick beer!! Great motorcycle destination!! Its on my ride list for sure!! Heard tell it that Neil Young pops by now and then for a jam session!! read more

Pioneer Saloon - Ohhh my goodness!! What a find!! - Dive Bars Near Me - Woodside, California

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This is a review for the Sunday Jam only, always the same people and not very friendly. I am in the area with friends often, so I have been to this spot many times . If you are not a local blues musician when you sign up, prepare to be ignored. A friend wanted to sign up and when he asked about the wait some guy Crawdaddy, gave us attitude. This Angelo guy always has an entourage of the same groupies taking his huge ego over the top. My friend is a touring musician,we just got back from NAMM . So we looked this Angelo up, old wanna be rock star, no wonder he did not want a pro to steal his dusty spotlight, avoid this jam and go to the Monday Night in Sunnyvale where everyone is welcome and there are actual crowds. I will come back on other days and tip generously because the staff is really nice and make up for the locals that don't tip. read more

When I was in college, my friends and I used to stay at my friend Kip's house in Atherton and do the Triple Crown of drinking as he knew all of the copless back roads through Woodside/Menlo Park/Atherton so we wouldn't get pulled over and busted. And Kip actually drove best the drunker he got which was plenty wierd. Wierd but true. If he was sober his eyes would be all over the road looking for girls but when he had a few in his gullet, his concentration to the roadway would be much more focused. Good for all concerned. Our Triple Crown was to drink at The Oasis and eat a pizza, carve your name in a table or wall, then move on to the Dutch Goose, drink some more, eat a burger with some deviled eggs, carve your name on a table or wall (do we sound a little like male dogs marking their territory? well that is kind of what we were doing, I guess) and then finishing up the night at the old low-class Woodside dive bar, the Pioneer Saloon. Although personally, looking back on the situation, why did we wind up the drunkest at a place farthest away from his house? Stupid drunks I guess. Anyway, I always liked the Pioneer best because of the live music and it still holds a fun place in my mind because of that. Beer and shots, but nothing for us except hard booze. Glad I don't drink anymore, jail is too tough and I've moved on to a much better place. Plus, hangovers so bad you can't lift your head off of the pillow just isn't worth it to me and I missed plenty of New Year's Day football games because of my pre-celebration habits. "Did you drive home? No, I thought you did." That's time to quit boys and girls, so I did. You will also never know who you will run into here. Billionaires. Movie stars. Rock stars. "Did you drive home? No, I have a chauffeur." Different lifestyle allows for prolonged alcoholism, I suppose. They all come to listen to the mostly country music, 'cause it is really hoppin' when the bands are rockin'. The dancing floor is often very crowded which I like and it can get pretty hot when the dust gets kicking up. The P.I. is a truly hidden gem that I wish never got publicized in yelp, I kind of liked P.I. when only a few people knew about it. So, read this review, then forget all about it. And if you are not a beer or booze person, you can still go to the Pioneer, have a coke or two and listen to the bands. Great fun for all. A date place only if your S.O. likes it down and dirty. read more

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! read more

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. read more

Great place but without warning they will have a private party and after driving all the way there ... it is close for a private party. Would be nice if they announced it on their website. This happened to us twice. Three strikes you're out. None of us are ever going back. read more

This place is divey - with live music playing and the dance floor of the Saloon has some undeniable old school charm. I have been to this place few times and have friends who had also frequented the saloon on various occasions. One thing which will spoil your mood for good is the service. The bartenders are the worst of their kinds you would ever fathom. Not only they are rude but they stoop down to the level of lying and use inappropriate remarks. Last night, three of our girlfriends went in to enjoy some country music. We ordered some drinks and sat down on the bar. One rugged older man walks up, touches on the arm and says to give up the stool as he was sitting. Although we did not see him being there when we came in, out of politeness we gave him benefit of doubt and gave up our stool. We went to the dance floor and when we returned, the man was gone and we sat down with our drinks on the bar stools. After 10 mins he comes back and asks for the stool back again. He was pointing to an empty bottle of beer and said he had paid for that stool and that was his drink that he left on the bar. This time there was no doubt left this man was trying to push us over. There are all kinds of people who visits bars and saloons. But to our utter surprise the bartender had started misbehaving with us taking his side. When he explained him the situation, He went to the extent of saying if we ladies had any education or etiquette we would give up our stools. We were 3 respectable ladies working in the Silicon Valley and execs in Tech. We could not believe our ears which were on fire by then. We did not want to spoil our mood further and decided to step out after the next song ends. When we picked up our bags and started leaving, the bartender in a very loud voice kept of saying BYE BYE BYE. It's a little bit of walk from the dance floor area to the main door. When we walked out of the front door, we could still hear him screaming Bye bye.. Before this I had never checked out the reviews of this place, but now that I read few of them. I could see all these are related to bartender being rude and misbehaving. Are we all crazy to have witnessed these horrendous services at different times or this place could actually use some help with training their staff better? read more

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. read more

This was the best place ever tonight their band was awesome. Couldn't pick a better place to go on a Friday night then here. The band was jammin and the bartender was on it. Fun music fun crowd!! read more

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! read more

Okay, I read the other reviews and even though it has been a few days (or weeks or more!) since I was last there, I can see the truth in those reviews as well as my own experiences of being there in person. Yes, it is a nominally quiet little local bar, during each and every day, but it can attract all kinds of 'Cowboys/Cowgirls' of course, usually as the day passes into evening and on to the midnite hour. Hours are usually 3PM to 2AM, when it usually closes with a 'Bang', depending on who the Band was that nite! The 'Bang' being "The OBS" (the Orange Blossom Special) or "The Devil Went Down To Georgia", or some other hot Country-Rock hit!) However, the Band doesn't start playing until about 9:30PM. By then, the place is usually Standing-Room Only! Cover after 8PM, Th/F/Sat. No Cover charge usually Sun/M/T/W. However, depending on the Band, S/M/T/W could be a VERY hot nite! Back to the 'atmosphere'. This is a local Country bar, and your cowboy/cowgirl boots are welcome here, even if you've been 'squishing' horse/cow 'patties' out on the range or in the corral all day! And Yes, very casual 'attire' is apropos! If you want to 'dress-up' fancy and do the Texas Two-Step or the 'Electric' Dance, go to the SaddleRack in San Jose, where they got the music and the dance floor for such. The dance floor here at the Pioneer is postage stamp, but that doesn't mean that it can't get crowded with 20 or more couples when the music is 'right'! Oh, almost forgot the most important thing! The Music! Okay, we'll say that it varies, mostly C/W, or C/Rock, or Hard Rock, or R&R, R&B, Blues, Folk, and maybe even some Hip/Hop! Can't say exactly what Bands are on the schedule for lately, but let me reminisce here a-bit! The Pioneer's 'house band' used to be 'Whiskey Hill', but they changed their name, but they're still playing the good ole 'sounds-as-usual'! 'Billy Band' was (and presumably yet is!) one of the Best C/Rock Bands around. Another great Band, almost every week, 'The California Cowboys', who usually play the SaddleRack on weekends, and have opened concerts for the likes of Willy and Haggard! Folk and pure C/W, as well as Blues and other genres, can find excellent 'rendition' at the Pioneer! Okay, people! Yes, it can get rowdy and drunks are not uncommon! (One night the parking lot was full of Harleys, 'cuz the Pioneer was full of Hells Angels!) But the 'quintessence' of the Pioneer 'experience' is not only local, and not only Bay Area wide, but national and international! Okay, it is true, some of the locals live just up the (country) road! Joan Baez lives just a short way up the road, and so does Neil Young! I remember twice (2 different times), when the table next to me in front of the stage, was occupied by Bono and the U2 gang, who had stopped by on a Tuesday nite to 'sit-in' on Billy Band's excellent sounds! Madonna, Joan Baez, Neil Young, Steve Young, Joe Montana, '49er's and all kinds of other celebrities! And Yes, as I said, the dance floor is small, but one night I was 'bumping butts' with Madonna! Another nite, I was 'bumping butts' with Shannen Doherty (of 90210). All kinds of folks, from everywhere and anywhere! My only warning: Beware if you are a health-nut or don't smoke! THIS IS COUNTRY, folks! At intermission time (usually about 11PM!), when the House Bouncer opens the rear door for some air, the accumulated smoke from hours-upon-hours of being cooped-up in that small space (UNLESS they might have gotten a bigger air conditioning!)... the smoke just pours out of that rear door at intermission time! I've met lots of gals and good folks at the Pioneer! Loni Anderson, the Actress, and a Female CEO of a company in Seattle... actually, never did get the name of that... WOW! But her big, black limo was parked just outside! But she was most friendly and most 'convivial', for sharing a small public table in a small public place! Anyway, even though I haven't been there recently, I'm going to give the Pioneer 5 Stars, 'cuz every one of my nites spent at the Pioneer, has been 5 STAR! Oh, it is best to Call, to check on the Band and Cover, for any nite! Incidentally, the famous Village Pub Restaurant of Woodside, is practically next door, so the Nite-of-Dinner-and-Dancing is a Reality. (Unless the Village Pub is hosting an International Peace Conference between... What was it lately? The Syrians and the Israelis? as they seem to have been in the News, lately!) read more

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! read more

Growing up on the Peninsula, I used to LOVE coming to the Pioneer Saloon to hear live music. Especially Monday nights when "The Buzz" would play every week (this is dating me a little as this is going on 15 years ago now). I now live up the road a little (no, not in Woodside!) and recently dropped in for an adult beverage on a Friday night on the way home from dinner. The place was as quaint and intimate as I remembered, but the clientele was a lot edgier than I recalled (guess I'm old.) There was a guy who was super f'd up making all sorts of passes at the young female bartender, who did her best to stay professionally courteous. It was uncomfortable. This is a great place to see live music though (and there aren't that many left on the Peninsula) as it is SMALL and sometimes LOUD. I love that. Only problem is, if the band sucks, and you get leave, it's like someone leaving your living room in the middle of a dinner party... it's that small. I wish I could give the Pioneer higher than a 3, but I need to retain a smidgen of credibility. Thank god it's a California Historical Landmark, so that it won't be going away any time soon (I hope). read more

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 ole' rock music. Will definitely return ANY and EVERY time I'm in the area! read more

A dive bar, in Woodside, within walking distance to my parents house? I just blew apart my AWESOME-Meter. read more

First time I went here, was because of of our friend's band GIG. We thought the place was cute and cozy. It felt so much different than the usual city vibe, which was a good thing.. However, what turned me off is the crowd, who were purely G-L-A-R-I-N-G, at us, because we were Asians. I understand that people there knew each other, but mind you, they don't own the bar for them to give attitude to new customers, because with the way they were acting that night, it just proves they are no better than just any new person who was there, that night. . read more

Decent bar. Especially divey for being in the heart of Woodside. It is usually pretty quiet except on weekends when they have bands play and there is a cover charge. The building itself is an old historic building (something like 120 years old) and the interior certainly has that old feeling read more

I like drinking at The Pioneer. I love how the inside has that "old timey" feel to it. The bar tenders are always awesome especially Meredeth (sorry if I misspelled that). I've had the pleasure of seeing a few good bands here. You can always check their website ahead of time to see who's playing. It does get a little loud but it's a really small room that's basically a rectangle with wood paneling on the walls and ceiling. Super reflective environment for the sound to bounce everywhere. I've had great times dancing with many pretty ladies on a packed dance floor to a good band. Seriously I cannot believe that The Pioneer is being rated lower than the Villa Roma. That place is a serious s**t hole and a great place to get a DUI. read more

We stayed at the bar for 15 minutes waiting to be served. The guy who is bartending ignored us. We waved. We smiled. After waiting long enough we left. Paid five dollars to get in. Will never go back again. Go somewhere else. We will never go back. read more

Ok here's what y'all missing and why. The real event is the Sunday Blues jam. For some of you the reason why it's 'hit or miss' is because the talent is 'hit or miss'. If you're looking for the ultimate non-pretentious atmosphere this side of the Rockies (I literally mean that being here in silicon valley), look no further than the 4-8 (closer to 6 actually) Sunday blues jam. Why? Because they just don't do the blues. It's bringing together the finest entertainers and seasoned musicians around in one place to dance, drink and holler to. It'll unify yer spirit and make you proud to be an American! once you come you won't want to leave until the band does. See you at the Pioneer and you can buy me a drink as thanks! I'll have a silver horn or guitar around my neck :) read more

I have not been here in 15 years but I do remember GOOD TIMES! It was a nightly tradition after work to go here for beers and shots. Nice that I was able to drink here at the ripe young age of 19, sure times have changed and the new generation will not be as lucky. Great dive bar in the middle of Woodside. I may have to go back and see if the bands are still playing. read more

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. read more

Great that woodside still has a dive.Mixed crowd,Great place for a drink after work,live music can be great or poor,if it is a night with live music check band out first. read more

Random, random, random. I love the Pio. Great dive bar that can morph from one thing to another in a night. Great live music, friendly bartenders and a local crowd. The only pain is that it sucks LEAVING the Pio. Be warned. TAKE A TAXI. read more