Cutest place to stop by for a sweet treat or a great meal! Staff was very patient and friendly. I got a lettuce wrap burger and fries. Honestly great burger. Fries also hit the spot. Diet Coke had the crispy crunchy ice. Finished off with the swirl soft serve. That was the best I've ever had. Very casual spot with plenty of seating. I can't wait to go back!! read more

Jumbo's Win Win - Soft serve - Burgers Near Me - Philo, California

Made a stop up here on the way to the Mendocino coast and while wine tasting at the many vineyards on the road. Ordered the Jumbo's burger (single) and the pickle dog. The burger was pretty straight forward. Ordered it spicy and it was indeed spicy!! Felt like the iceberg in this somewhat watered down the richness of the meat and I might elect to get a double or the Okie Onion smash burger should I make my way back. The hotdog had a bunch of pickle jalapeño relish which made it quite wet and cold. Was also missing the characteristic snap of a good sausage. Otherwise appreciated the brightness of pickle and mustard. Both items came out lukewarm. I might not specifically make my way out to come here but works well if you're passing through. read more

Jumbo's Win Win - Jumbos burger - Burgers Near Me - Philo, California

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Finally... finally... FINALLY stopped at Jumbo's Win Win in Philo. Headed back to Bay Area early after a stay on the North Coast, and the magic formula for not wading through the ever present lines and crowds at this roadside institution seemed to be a midweek lunch stop. Maybe 6 people total already there. Walked in and gave the menu a quick look over. There's the regular menu plus a few specials listed to the side. Wine, beer, and soft drinks available on a menu near the register. It was a toss up between the Jumbo Burger or the Okie Onion Smash Burger. After some advice from the friendly counter person, I went with the Okie Onion Smash Burger, double patties. Husband ordered the Chicken Karaage special. Bottled sparkling water and a Pliny the Elder brought us in at $42 tab (plus tip). We grabbed seats in the garden out back with was super pleasant with lots of tables, chairs, and fun artwork. You could even ride a hippo or a giant tortoise while eating if you're so inclined. Food was brought out to us (normally they call numbers, but it was on the quiet side today). My Okie Onion Smash Burger was huge. Grilled onions, melty cheese, double patties, and generous portions of crisp iceberg lettuce, pickle, and tomato slices topped the meat, and the toasted brioche bun was slathered with a thousand island-like spread. I was able to use my hands for about half, but had to resort to a knife and fork to finish it off. A delicious mess! Husband liked the chicken karaage, but they were more chicken nuggets than karaage. When I think of karaage I think shatteringly crisp pieces of chicken in a light potato starch breading. This was more cornmeal breaded and fried. Good, but not quite karaage. No complaints tho as it was also delicious with the spicy mustard. Didn't order fries or ice cream this trip, but that's what the next trip to Philo is for. What's left to say? Great food. Great drinks. Come off peak hours for an easy in and out experience. Def a must stop! read more

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Such a great pitstop for food along the highway! Friendly service and plentiful indoor and outdoor seating. - Onion smashburger: loved the potato bun and the burger was properly sauced up. The onions and pickles were delish in this! - schwinger fries: perfect combo of fluffy and crispy!!! Loved these - soft serve: creamy but also light, such good flavors in the greek toppings - the fennel was delightful! read more

Jumbo's Win Win - Onion smashburger and fries - Burgers Near Me - Philo, California

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We stumbled across Jumbo's during our drive back from Mendocino. We drove past it, but saw some people go in and we turned around and decided to get some food. The exterior and interior of this shop is super cute! Love the diner feel of this spot. The line to order was short and we thought ok, it shouldn't be too bad of a wait because the line to order was short and it's burgers and fries, so it shouldn't take too long. We ordered one Jumbo's burger (single), sidewinder fries and pickle beer. We didn't want to order too much since we were just driving back home and wanted a little "snack." We ordered at 1:53 pm and didn't get our order until 2:50 pm!! During that wait, we were getting very impatient. We got our food and ok.... We were blown away. My boyfriend and I were just so annoyed and we were just like, this better be worth the wait and well...it was worth the wait. So, knocked down one star, other than the wait, would've been a five star spot for us. Can't wait to come back to this spot! read more

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This looks like your typical roadside diner but it's on another level. The burgers are first rate and could be found on top ten lists. Its slick interior, hospitality, and fun atmosphere are a plus. I had an excellent smashburger with cheese, grilled onions, pickles and just the right amount of edge crispiness. The fries are excellent. They have a nice variety of beers, wines, plus an irresistible soft serve ice cream. Don't pass this one by! read more

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A MUST stop, burger (and more) diner on the 128! Smash burgers were cooked perfectly and the hand cut fries were some of the best fries I've ever had. Topped it off with a soft serve ice cream in the back patio area. Will be making this a stop every time I'm on the 128 read more

Jumbo's Win Win - Burgers Near Me - Philo, California

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Food is amazing! Stopped on our way back from Mendocino and we were so impressed. Great vibe local ingredients (& local people) and can't wait to go back! read more

Stopped here along the way to Fort Bragg for a quick stop and bite to eat. I heard this place had great smashburgers despite being in a remote area on Hwy 128. But news spreads fast and here I am. We both enjoyed the okie smashburger and Jasper fries. The burgers were juicy and had lots of flavor. The grilled onions and pickles were a nice touch. The fries were great too. Crispy and I could tell by the taste they were fresh organic. The pickle beer was a first for me... and the other reason why I wanted to check out this spot. It's interesting. You get hints of both pickle and beer at the same time. It wasn't that bad actually. Overall this place is a hidden gem. You can eat inside or outside and enjoy the beautiful scenery of the Alexander Valley. The outside seating area is pretty nice. I wish I would've got the name of the cashier because she was very friendly and helpful. Makes everyone feel right at home. I would definitely make this my go-to stop whenever I'm headed to Mendocino County. read more

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This is a very nice place to stop and have lunch. It's very clean and they have nice music playing. The service was great, you order at the counter. They have outdoor seating, and I heard the waitress say they were having a superbowl party which I am sure would be a blast. I got the jumbo burger and it had high quality meat with fresh veggies and a delicious bun. The special sauce tasted like it might have horseradish in it. The root beer was amazing and hand cut fried are very good. I ordered the hand apple pie to go and it was made to order and excellent. I would highly recites place. read more

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Stopped here for a quick bite on the way to Mendocino. Cool little spot with nice interior, self-service setup, and some outdoor tables too. We tried the chicken sandwich, pickled beer, fries, and soft serve, one plain and one with fruit. Just FYI, the sandwich doesn't come with fries, it's $14 by itself, fries are $5, beer $5, and soft serve $5 (extra if you add fruit). The chicken sandwich is hands down the star, super juicy, crispy, piping hot, with a toasted bun and finger-licking sauce. Worth trying at least once, though $14 feels a little steep. Fries were solid, some a bit on the thicker side but still good. The soft serve was a miss for us, not great flavor, and the fruit topping was more like a jam, which was kind of off-putting. The beer is very interesting and my family liked it very much. Overall: stop in if you want a quick snack and definitely go for the sandwich. Just skip the soft serve. read more

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This was the perfect stop on a long roadtrip: I can't believe how fresh everything was given that they're kind of in the middle of nowhere. The Greek style soft serve was my absolute favorite and they make a mean smash burger too. I had also never seen fries in this shape and I can understand why they are so popular now! Look forward to trying more on my next trip. read more

Jumbo's Win Win - Burgers Near Me - Philo, California

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Overall this place is very interesting and the food is pretty good. I wanted something on the lighter end so I got the wedge salad (half size) but I couldn't finish it because there was way too much dressing. I was impressed they were able to get the dressing in between all the layers of the lettuce. This would be great for those who love extra dressing but it was just too heavy for me. But I did love the flavors overall and everything that was put into this dish. The soft boiled egg, the chives, bacon bits, pickled red onions, etc. It gave a slight Asian flavor to it, which I enjoyed, but again, just too much dressing for my personal liking. The restaurant was pretty big and had ample seating inside and out. There were a few flies hovering over the tables inside though which was a bit annoying. read more

Jumbo's Win Win - Wedge salad - half size - Burgers Near Me - Philo, California

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This is a must-have spot on the way to and from the Mendocino/Fort Bragg area. I heard about the place on social media, so we stopped here for lunch on the way to Mendocino. After having the food, I knew I wanted to stop again on the way out. The first stop was about 2:30, and it was still fairly busy. There was a small line, which was fine cause it gave me enough time to choose what I wanted. I ended up trying the single Jumbo's burger (my partner also got a single Jumbo's burger) with one order of sidewinder fries. We had also ordered the apple hand pie and the seasonal hand pie (which is currently quince). It took about ten minutes to get the food, which was enough time for us to grab a table inside (there is also plenty of outdoor seating), use the restroom, and admire the decor. Our order was called out by number and we went back to the counter to pick up. Our food was on a tray, with notes on the parchment to let us know which burger was which and which hand pie was which. They had set out paper plates, napkins, and condiments on the bar for self-serve. The food was so delish! The burger was perfectly cooked and the sauce was great. The sidewinder fries were crispy on the outside and soft inside; they kinda reminded me of a Korean tornado potato but thicker. The hand pies were so good. I'm not a dessert person but I'm a sucker for apple hand pies and this was no exception. The seasonal quince was tart but it went well with the flaky pastry. Our second time trying Jumbo's Win Win was on the way out and the line was significantly longer! We waited about 15 minutes to order, but once we got to the front, the ordering process was quick as well as getting our food. This time, I ordered the fried chicken sandwich, and it was my favorite of all the things I'd tried from there. It was Tokyo-style (so like karaage chicken) with a slaw that perfectly cut through the fried heaviness. I absolutely would stop by again for that chicken sandwich. read more

Jumbo's Win Win - Quince hand pie at top left, apple hand pie on bottom left. Sidewinder fries, and two single Jumbo's burgers. - Burgers Near Me - Philo, California

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I just went there yesterday. My friend suggested it, she read about an article that a person or family moved from SF to Philo and open this cute restaurant. 1) Decor is modern cute farmhouse. The bathroom is really nice 2) There are indoor seating and outdoor seating. 3) Yesterday is holiday, labor day monday. I saw a music band setting up to play. I go to run. 4) food is very good. My friend said you could customize your burger to have some jalapeno chopped and put on the bottom of your burger. Super tasty. 5) I got burger one piece of beef, very good. 6) my daughter got chicken sandwich and also soft serve. 7) a lot of parking, don't let the front discourge you. There are a lot of parking at the back. Highly recommended, will be back again. read more

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Jumbo's Win Win was such a pleasant surprise! We came in for lunch, mostly due to its convenient location. The interior had cool, retro decor and was dog-friendly. They also had a large outdoor seating area in the back, but that had quite a few bees. There was no line to order at the counter, and all the staff members were super friendly. I got the Smashburger with Jasper's hand-cut fries, which were fantastic. The Smashburger was almost perfect (except for the excessive mustard). I don't usually prefer thick fries, but these had a great texture. We also asked for the house-made chili aoli - highly recommend trying this with your fries! My friends all enjoyed their food as well, including the Fried Chicken Sandwich and Fish Tacos. I couldn't resist also getting Vanilla Ice Cream with their house-made Blackberry Compote (seasonal). The compote was made with locally picked blackberries, and completely rocked my world. It paired so well with the soft-serve and tasted incredible. This place is a gem! read more

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Awesome throwback spot, our new go-to when we go to the coast! Burgers are tasty, fries are hot and fresh, soft serve can't fail and they have fun toppings! Awesome seating with a view of the hills around Philo, plenty of space with animal sculptures the kiddos can climb on. Staff are super friendly, and they have wine and beer on tap. Bathrooms are clean and they even have a buck hunter video game. This place is so legit! Can't wait to go back. read more

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So fun to stop into Jumbo's for a quick bite. Super cute place with a menu to please- burgers, fries and soft serve. The service is fast and friendly and lots of drinks to choose from too. We went with the vegetarian quesadillas and veggies open face service. Make sure to get the sidewinder fries. Enjoy! read more

Jumbo's Win Win - Veggies abound and those sidewinders! - Burgers Near Me - Philo, California

Wow! Wow! Wow! Wow! Wow! A wow for every star. Lauren. Food. Atmosphere. All of it. Some of the best i have ever had. read more

Jumbo's was a great stop when heading home after a weekend in Mendocino! We ordered the smash burgers and they were absolutely fantastic! The buns were so soft, the meat was juicy, and the fries were fried to perfection! The service was very quick, and the vibes of the restaurant were really nostalgic. Would definitely go back if Im ever in the area. read more

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Jumbo's in Philo is a full-blown roadside miracle disguised as humble burger shack. It doesn't scream for attention, but it absolutely deserves it. This place serves up the kind of burger that makes you roll your eyes in pleasure and question why you ever settled for fast food mediocrity. The patties are juicy, seasoned just right, and stacked like they mean business with fresh condiments, melty cheese, and buns that don't fall apart mid-bite (because we're adults here, barely). The fries are golden perfection, best I've had in a very long time. They also have gargantuan hot dogs, chicken sandwiches and more. Jumbo's is the real deal: no pretentious menu, no overthought branding just unapologetically good food served up with small-town realness. Sit your happy butt down at a picnic table, breathe in that Philo country air, and devour something that actually satisfies. It's the kind of spot you brag about discovering but secretly hope never gets too popular. Because Jumbo's isn't just a burger stop it's a glorious rite of passage. You came for the food, but you'll come back for the feeling. And maybe a second burger. read more

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We stumbled upon Jumbo's Win Win with 0 expectations and left completely BLOWN AWAY! My husband declared their burger one of his top 5 ever - juicy, flavorful, and perfectly cooked. The fried chicken sandwich? Equally phenomenal. We'll be thinking about it forever and ever. Their fries were crispy and fun shaped, almost like the size of waffle fries. Also tried the Chopped Salad, which was solid as well. The drink selection is pretty big for a diner, including a tempting pickle beer. It looked like the perfect pairing with their burgers. The interior has a mix of nostalgic diner charm and modern chic. We got our food pretty quickly as well. We were honestly so impressed with the food that we're planning our return trip from Mendocino just to eat there again. If only it were closer to San Francisco! What an absolute gem!!! read more

Good here is always a win win. Burgers are classic. Chicken karage is a great take on chicken tenders. And they have great sauces. Must try their weekly socials they have an amazing selection eco always today I had the fish tacos. Yesterday I had the aguachiles Ama they were spectacular. Try the pickle beer it's always great. read more

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Best burger spot in northern california. With a wicked chicken sandwich to boot. Perfectly crunchy fries. It's obvious they care about each detail and benefit from the local farms and ranches close by for the freshest ingredients to make even a simple hot dog out of this world. Friendly staff with the perfect balance of a retro diner proud to be in the hyperlocal community of Boonville. The pickle beer is fun to try, other excellent and well respected beers on tap as well. We come to Anderson Valley often and this is now a must stop each time, can't wait to catch live music on their epic redwood stage next time. read more

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Amazing stop on the way up to Mendocino. It's incredibly spacious, service was friendly, and the food was phenomenal. Ordered Jumbo's burger, hand cut fries, and greek style soft serve. The salt, olive oil, honey, and fennel made the vanilla soft serve remarkable. The fries were triple fried making them taste like yucca fries; extremely crispy on the outside, and airy yet starchy inside. The burger was one of the best I've had. The sauce, lettuce, pickles, onions, tomatoes, and beef patty were all in harmony. It puts all the burger spots in SF to shame. I forgot to ask to make it spicy, but will hope to get a chance in the future to visit again. read more

Jumbo's Win Win - Jumbo's burger and hand cut fries - Burgers Near Me - Philo, California

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I've been wanting to try this place for so long and it absolutely exceeded my expectations! I shared the fried fish sandwich and the Baja shrimp tostadas (from the mariscos menu) with my sister, and everything was outstanding. My mom has celiac and she was able to enjoy a variety of gluten-free options. They even have a separate fryer for the fries so she could have those safely. And don't forget the soft serve! We all had The Greek soft serve, and it was hands down one of the best things I've ever tasted. I honestly felt sad when I took my last bite because it was so delicious. The interior is adorable--even down to the bathrooms! The design really adds to the overall experience. The staff, especially the man who helped us, was incredibly kind, attentive, and helpful throughout our meal. There were so many other things I wanted to try so I can't wait to come back! read more

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Such an unlikely place where I had one of the best smash burgers of my life! As soon as you walk in, you're greeted by the very snazzy retro ambiance and decor. The menu has plenty of options (burgers and non burgers). The burgers tasted super high quality and weren't too greasy. Fries were excellent too! A must visit if you're in the area! read more

Jumbo's Win Win - Smash burgers, regular burger, assortment of fries, and a fruit hand pie. - Burgers Near Me - Philo, California

We stumbled upon this gem on our way to Mendocino on a VERY rainy day. We were met by Molly, the owner, who was SO nice and so helpful. We decided on a Jumbo's burger for me, an open-faced veggie melt for her, shared a 1/2 chopped salad, a glass of local ale for me, and a glass of Sharffenberger bubbles for her. The burger was amazing with a wonderful bun, perfect meat, and crisp vegetables. The veggie-melt was to die for. It was perfect. The drinks were super cold, and of course we had to share a soft-serve ice cream on the way out the door. This is a MUST go to place when in the area. We will be back!!! read more

Jumbo's Win Win - Jumbo's menu. - Burgers Near Me - Philo, California

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Clean, efficient, affordable, delicious, small but nice drinks list... what's not to love? A smashburger oasis on your way to the coast! (Be sure to order the fries extra-crispy and they'll be among the best you'll find anywhere) read more

What happens when a SF bar legend opens a modern Americana diner in the heart of Anderson Valley? Pure magic, that's what. Jumbo's Win Win, helmed by Scott Baird (co-owner of SF's acclaimed Trick Dog), has become my family's mandatory pit stop between wine country and the Mendocino coast. So mandatory that we ate here THREE times in one weekend during our mushroom foraging adventure! The setup is refreshingly simple - order at the counter, then prepare for some of the best casual eats you'll find in Northern California. The menu is focused and intentional, spotlighting local purveyors and organic ingredients whenever possible. Let me break down the must-orders: The burgers? Perfection. The fries? INSANE (seriously, don't you dare skip them). But the sleeper hit is their mind-bending soft serve topped with honey, olive oil, sea salt, and fennel pollen - a combination that sounds wild but works brilliantly. We've basically eaten our way through the entire menu at this point - stellar chicken sandwich, fantastic fish sandwich, and surprisingly crave-worthy salads. The rotating specials keep things interesting, and the drink selection is on point (would you expect anything less from a Trick Dog alum?). What really seals the deal is the vibe - it's that perfect blend of local hangout and traveler's oasis. You'll see regulars catching up at the counter while road-trippers like us plan their routes specifically around hitting Jumbo's for lunch. Pro tip: If you're heading up to Mendocino or exploring Anderson Valley, this is your spot. The quality and execution put most big-city spots to shame. Just don't blame me when you find yourself making excuses to drive through Philo just to grab another burger. One last time for those in the back: DON'T. SKIP. THE. FRIES.​​​​​​​​​​​​​​​​ read more

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Food and service were on point! On our trip back home, we found this quaint but popular spot to enjoy our lunch. Outside patio area was really nice. Weather was perfect. read more

Stopped twice in 3 days. Food was excellent. First time we tried the onion smash burger and el.reuben... where the meat is steeped in birria juice like.the quessabiria tacos. Both were excellent. And of course the fries were to die for. Second time on the way out of town with friends. This time fish tacos and the crispy chicken sandwich. And more.fries My husband would have had the Reuben again, but it was.sold.out! For me,.the.smash burger and fries were the star... the Reuben for my husband. Definitely worth visiting!! read more

Jumbo's Win Win - Smash burger with fries... yum! - Burgers Near Me - Philo, California

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I don't review often on here which should show you how good I thought this place was. Despite being slammed and having limited staff, the food came out quick, hot and oh was it delicious! I went with the Double Okie Onion Smash burger. One of the top three burgers I've ever had. SOOOO GOOD! The Fries were on point--crispy, nicely salted and hand cut. We got soft serves for the little ones that also were a hit. All in all an amazing dining experience. Looking forward to going back soon! read more

We drove about an hour and a half from home just to visit Jumbo's! When you go in you have plenty of time to browse the large wall menu before you give your order and pay, however there was a specials menu and an additional menu with Mexican food options that you don't see until you get to the cashier! So helpful tip, walk up there and take a photo of the extra menus to look at before you decide! The restaurant has a ton of seating, indoor and outdoor. You seat yourself after ordering, then they call your number when food is ready for pickup. The pickup counter was spotless and had all the utensils and condiments. Food was great! I enjoyed the open-faced Mixed Veggie melt very much! It uses cheddar and Gouda cheeses, atop sourdough bread. Delicious! It was flavorful and filling! Don't forget dessert, the apple hand pies are great too! I saw other menu items I'd like to try, so will definitely make my way back to Jumbo's. read more

Jumbo's Win Win - Mixed Veggie Melt, Smash Burger with Sidewinder fries, and apple hand pies - Burgers Near Me - Philo, California

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Delicious food, charming vibe, and excellent service. And affordable! No wonder this place has become a wine country winner already. #punintended pro tip: the line to order is long but then your food comes out nice and fast - super worth it. read more

Jumbo's Win Win - El Ruben birria pastrami sandwich with hand cut fries 12/10 - Burgers Near Me - Philo, California

We visited on Sunday afternoon and found parking right away. We ordered the Fried Chicken burger - the chicken was crispy with the kewpie mayo and lettuce was perfect and the fries were crispy and well seasoned. I really liked the root beer with the crushed ice. The ambiance was cute and I liked the outdoor seating. read more

Jumbo's Win Win - Fried chicken sandwich and Jumbos burger - Burgers Near Me - Philo, California

Jumbo's Win Win was an absolute win! We came across the diner after a trip to the goat farm up the street. JWW was so good! My burger was probably one of the best ever! The cashier was so sweet! The diner was very authentic! We will be back! read more

Stellar grub and casual diner vibes. Popped in on a rainy Sunday evening after a day of wine tasting Anderson Valley's finest. You order upon entering and grab a seat at one of their cozy booths. Upon recommendation, I ordered the fried fish sandwich with a side of sidewinder fries. For $20 (food+tip) you can eat Phenomenally! The fish sandwich was perfectly breaded, light and flakey, and the fries ticked all the buckets! Great vibes and reasonably priced, good food - what more could you ask for? read more

Jumbo's Win Win - Fries fish sandwich with sidewinder fries - Burgers Near Me - Philo, California

I always pass this place and have wondered how it is. Finally stopped in and, Well it's great! My husband and I split the Fish Sandwich & the Double Smash. Both were delicious. Service was great as well. We went back for dessert and got the Lemon Curd soft serve & The Greek.... Also delicious! We will definitely be back. read more

Come for the burgers, stay for the Mexican food! Their burgers are the best we've had anywhere. The patties are thin and grilled to perfection. There's probably not much I can say that hasn't already been said about this iconic local establishment. We come here at least once a month. Tip: you can get the burgers animal style (keto friendly) with lettuce instead of buns. read more

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