Things to Do in San Jose in May
May weather, activities, events & insider tips
May Weather in San Jose
Is May Right for You?
Advantages
- Perfect spring weather with temperatures around 25°C (77°F) - warm enough for outdoor activities without the brutal summer heat that hits in July and August. You can actually walk around downtown midday without melting.
- Shoulder season pricing means you'll save 20-30% on hotels compared to peak summer months. Most mid-range hotels in downtown run $120-180 per night in May versus $180-250 in July, and you'll have better availability without advance booking.
- The city comes alive with outdoor events and farmers markets hitting their stride. The Saturday morning farmers market at Arena Green expands to full size in May, and outdoor concert series at various venues start their summer schedules.
- Minimal rainfall (just 25 mm or 1.0 inch typically) means you can plan outdoor activities without much weather anxiety. Those 10 rainy days are usually brief evening drizzles rather than all-day washouts, and they actually help keep the air quality better than the bone-dry summer months.
Considerations
- The weather can be genuinely unpredictable - mornings might start at 14°C (57°F) requiring a jacket, then hit 25°C (77°F) by afternoon. Locals call it 'microclimate roulette' and you'll see people in shorts and winter coats on the same street corner.
- May Gray is real here, despite what the tourism board tells you. Many mornings start overcast and don't burn off until noon or later, which can be disappointing if you're expecting California sunshine from sunrise. The marine layer from the Pacific tends to linger more than visitors expect.
- Major tech conferences start ramping up in May (Google I/O typically happens mid-May), which means downtown hotels get block-booked by corporate groups and prices spike during those specific weeks. If you're flexible on dates, avoid conference weeks entirely.
Best Activities in May
Santa Cruz Mountains Hiking and Wine Tasting
May is genuinely the sweet spot for the mountains just west of San Jose. The hills are still green from winter rains (they turn brown by July), wildflowers are blooming along trails, and temperatures in the mountains sit comfortably around 18-21°C (64-70°F) - perfect hiking weather. The wineries along Highway 17 and Skyline Boulevard start their outdoor tasting season, and you can combine a morning hike with afternoon tastings. Trails like St. Joseph's Hill or Sierra Azul typically cost nothing for parking, while wine tastings run $20-40 per person.
San Jose Downtown Food Walking Tours
The 70% humidity might sound uncomfortable, but it's actually mild compared to true summer heat, making walking tours through downtown neighborhoods very doable. May is when local restaurants start rolling out spring menus and outdoor patios open for the season. The SoFA District, Japantown, and Little Portugal neighborhoods are compact enough to explore on foot, and the variable weather means you can duck into restaurants or cafes if it drizzles. Tours typically cover 1.5-2.5 km (1-1.5 miles) over 3 hours with multiple tasting stops.
Bay Trail Cycling Routes
The Bay Trail sections around San Jose are excellent in May before summer crowds arrive and before the marshlands get their distinctive summer smell (putting it politely). The 20+ km (12+ mile) stretch from Alviso to Shoreline Park offers flat, easy riding with bay views and bird watching opportunities. Morning rides are particularly nice - that marine layer keeps things cool until it burns off around 11am. Rent bikes for $35-60 per day from shops near downtown, or bring your own.
Tech Museum and Innovation District Walking Tours
May weather is variable enough that having solid indoor options matters, and The Tech Interactive is genuinely worth 3-4 hours. But the real insider move is combining it with walking tours of the surrounding innovation district - you'll see the actual offices where Silicon Valley happens, not just the museum version. The outdoor plazas and public art installations around Adobe, Zoom, and PayPal headquarters are accessible, and the weather in May makes outdoor walking between buildings comfortable. Museum admission runs $30-35 for adults.
Alum Rock Park Hiking and Picnicking
This is San Jose's oldest park and feels completely different from the urban core - actual wilderness just 20 minutes from downtown. May is ideal because the creek still has water flowing (it dries up by August), the canyon stays relatively cool even when the city heats up, and the mineral springs area makes for interesting exploration. Trails range from easy 2 km (1.2 mile) loops to challenging 8 km (5 mile) climbs up to the ridgeline. Parking is $6 per vehicle, and the park rarely feels crowded even on weekends.
Winchester Mystery House Tours
Yes, it's the most touristy thing on this list, but May is actually a smart time to visit. The mansion is entirely indoors (perfect for those overcast May mornings), crowds are lighter than summer, and the gardens surrounding the house are in full bloom. The standard tour takes 65 minutes and covers about 0.4 km (0.25 miles) of walking through 110 rooms - all indoors with climate control. Tours run $45-65 depending on which option you choose, and the property is genuinely weird enough to be interesting even for skeptics.
May Events & Festivals
Cinco de Mayo Festival
San Jose has a significant Mexican-American population and the Cinco de Mayo celebrations here are substantial - not just token events. The main festival typically happens in the SoFA District or downtown with live music, food vendors, and cultural performances. It's worth attending if you're in town during the first weekend of May, though be prepared for crowds and street closures around the festival area.
South First Fridays Art Walk
The SoFA District (South First Area) hosts monthly art walks on the first Friday of each month, and May weather makes this particularly pleasant. Galleries stay open late, street performers set up, and food trucks line the streets. It's free to attend and gives you a genuine sense of San Jose's arts community rather than the tech-only reputation. Happens roughly 6pm-10pm.