Cool Bars in San Jose

Are you on the lookout for the most poppin’ Cool Bars in San Jose?

Then we have you covered!

On this page, you’ll find the official shortlist of the best Cool Bars in San Jose. (More in-depth further below)

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Old Wagon Saloon & Grill

Old Wagon Saloon & Grill offers regular happy hours with Texas barbecue, mixed drinks, draft beer, and Old West charm. The salon has an outdoor deck with a bar, beer pong table, live music stage, and cozy fire pit. There is also a collection of TVs inside, so there is no shortage of entertainment. After sunset, the Old Wagon Saloon even has an outdoor screen for watching movies. Hamburgers, ribs, Texas barbecues, and beers are served in a spacious tavern and outdoor patio decorated with Wild West. The Old Wagon Saloon is situated in the heart of San Pedro Square in downtown San Jose. The Old Wagon Saloon offers a cozy atmosphere and creates a modern bar with old western charm. The relaxing space is a great place to have a business lunch or spend the night in the city with friends. In addition to the bar area, there is a spacious outdoor heated deck and pet-friendly outdoor seating. All hardened meat is smoked in-house. Her smoker “Madame Stacy” is cheered on every day. Old Wagon Saloon’s cathedral ceilings, copper bars, and modern Western charm make it the perfect place for your next event. They help you coordinate all the details of your event to ensure it succeeds. Whether you’re on a business trip or private, they’ll meet your needs. They take reservations as well. So, if you need to book a table or a spot then feel free to connect with the venue page. Old Wagon offers delivery and takeout services. Masks are required to visit this bar due to the covid pandemic. All the staff wear masks as well for their safety and for the safety of the patrons. The menu at this bar has many vegetarian options. So, if you are vegan and visit the bar you wouldn’t have to worry about food options.

3rd & Bourbon

Can’t get enough industry-themed destinations? The 3rd and Bourbon (small but intimate spots) should be on the list. The bar’s menu, serving modern American cuisine, caters to a wide range of visitors. Rely on a classic burger and beer combination, or boldly with  Cajun chicken pasta, grapefruit, and thyme martini. As the name implies, the bourbon menu at this bar is also impressive—a cute bar with a wide selection of cocktails and food. Five stars for food, drinks, services, music, decoration, and prices are worth you. This bar offers a delightful experience! House cocktails are prepared experimentally, but they are very delicious! There is a small, cozy, and relaxing atmosphere on 3rd Avenue and Santa Clara Street in downtown SJ. It is also right next to Enzo. They have friendly and attentive staff. It also disinfects the table every time the customer uses it. They take reservations at this bar as well. So, if you need to book a table or a spot then feel free to connect to the venue page. This bar offers delivery and takeout services. Therefore, if you want to order your favorite meal with your favorite drink from this bar, you can do it! The staff wears masks because of the covid pandemic. So, they do this for their own safety and the safety of the patrons. The food menu at 3rd & Bourbon has vegan options as well. So, if you’re a vegan you will not have to worry about deciding what to eat. Although their vegan options are limited, still there are vegan food items available. They accept credit cards as a payment method. Outdoor seating is available for all patrons at this bar. We can safely classify this bar as Classy. So, it has a moderate noise level. They also offer catering services.

Shepherd & Sims

Jumping directly to the Shepherd and Sims cocktail menu will miss some of the magic. Take a closer look at the wooden ceilings with slats, vintage mirrors, rattan patio furniture, and murals of the foggy forest running one wall length. Try poached Spanish octopus sprinkled with smoked paprika oil or duck confit with toasted croquette meat, algra, and white cheddar for cooking. Homemade potato chips with French onion dip and caviar are also praised. But let’s move on to drinks. House cocktails such as Shepherd’s Pie and thyme waste provide various flavors. But we would like to make a special mention of the Italian Winters. So, this is a satisfying blend of rye, Montenegro, amaretto, lemon, and bitter. Here they celebrate diligence, a simple meal, and an excellent companion. This bar offers takeout services. The staff at Shepherd & Sims wear masks for their own safety and for the safety of the patrons. They accept credit cards as a form of payment. Outdoor seating is available at this bar. Heated outdoor seating is also available for when it gets too cold. So, if you wish to step with your drink, feel free to do so! We can describe the vibe of the bar as Hipster, Casual, Trendy and Classy. It is a great place for groups, kids and for dinner. They have street parking and private lot parking available at the scene. So, when you visit the bar, you would not have to worry about thinking where to park. They have impeccable waiter service. There is free Wi-Fi available at the bar for all the patrons. The best nights at this bar are on Thursday. They have Happy Hour Specials throughout the week. Shepherd & Sims provides wheelchair accessibility. There is a TV present at the bar which adds to the audio and visual experience of entertainment.


There’s a lot going on in the South Bay, and it’s not all about technology. The skyline of San Jose, the fifth largest city in the country, is changing, and more people are relocating Downtown. There are new activities, restaurants, and (most crucially) drinking establishments. We’ve selected the top cool bars and breweries to visit the next time you’re in San Jose. Leave your car at home; most of these locations are within a 15-20 minute walk of Caltrain.

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