Welcome to TAC! The website has some good observing site suggestions at https://observers.org/observing-sites/
I'm also relatively new (joined TAC 6 months ago or so) and in Sunnyvale, so pretty close to you. Here are a few sites to learn more about
very close options:
Your yard, front porch, or a friend's house
30min-1hr drive:
Montebello (see website for instructions)
Henry Coe Overflow lot (see website for instructions) - slightly darker than Montebello, but may be farther
Peninsula Astronomical Society has a site up in the foothills but I haven't visited yet
San Jose Stargazing Club is also near you, but I haven't worked with them yet
1hr-2hr drive:
Freemont peak (haven't visited)
Pinnacles West (haven't visited)
Tri Valley Stargazers sites (see their website for requirements) - Lake Del Valle & H20
3+hr:
Consider joining California Dark Sky Enthusiasts to use their research on sites (can't discuss locations here)
IHOP is back on the menu too at this distance, but there are darker options at the same distance by targeting HW108 (quicker way to get to Sierra Nevada from here) or going beyond Pinnacles to the south. Consider CDSE or Clear Dark Sky for inspiration on sites to try out at this distance.
Hopefully this helps get you started with some things to look into
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I liked Crestview Park. San Carlos. They had a street light blocked by the city that would have otherwise lit (at eye leve) the entire parking (observing) lot directly up the hill from it.
I consider this accomplishment up there with the great astro shows and venues of years past.
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Many like Coe, but the drive to it is a long winding road, so it actually takes a similar time than the drive to Dinosaur Point. Dino has darker skies to the South, Coe probably has darker skies to the east -- it's been a while since I have been there. Dino has wind in the summer. The downside is that the upper lot (which is the only one you can get to after dark) is in sight of the distant highway and sometimes people will come to the lot to do observing and they don't know to turn off their lights coming in. This is common during "events" like a comet or meteor shower that's been in the press. I have considered making a sandwich board I could put out to semi-block the entrance saying, "LIGHTS OFF, Astrophotography in progress. Have a pedestrian guide you in."
In theory you need to pay a park fee to park there, and I have a park pass, but I've never seen them ask. Coe also has a fee.
Note that Coe and Dino are 1 hour destinations so you can go, observe, and make it home after. LSA and Pinnacles are more camping locations for bay area people at 2 to 2.5 hours. Montebello is a 30 minute location for the south bay, so easy to get home. However, it has a fair bit of glow from the bay. Sempervirens point has darker skies to the South and West, but it is technically closed after dark. The cops will kick you out on weekends. They may not come by on weeknights. A group of muscle car owners tries to rally there on weekends and the cops come to kick them out and they also kick out the astronomers. There are other locations with the same issue.
The main downside of Montebello, other than the glow from the valley, is that you do have to get your permit in advance. Officially a few days, but in practice often same day. But you can't officially "just pop up there because the sky looks good" which would be ideal. Oak Ridge observatory would be the best place for that if want to pay the fee and get a place that's 35 minutes away.
Next time I am considering experimenting with this location:
https://maps.app.goo.gl/kqh3eieJpHAe1tiGA
It's quite dark, it's 1 hour 10 minutes (just a bit more than
Coe) and it's in the middle of a dry wash, so I am not sure if
anybody owns it or would kick you out. But I've never tried.
That's about the limit of how far to go if not camping. I also
considered the San Benito county fairgrounds but they said no, but
forgiveness might be easier than permission.
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Another good aspect of Crestview is the open treeless view over the soccer field to the south and south west. Besides 280 Freeway, there is nothing that direction in the way of lights clear out to the ocean. The small lot is also a roundhi about around beautiful redwoods to keep speeds to 5 mph. The sidewalks are large and accomidating. After soccer ⚽️ it's game on for night 🌙.
Welcome to the party Ash! In addition to many good suggestions above, I would also recommend to watch for OI (Observing Intent) posts on this list, esp. around the NM, and join a small group instead of wandering in the dark alone. At least for the starter. That's not only safer, but also helpful for a newcomer to get oriented around.
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One couple would drive 60 miles from East Bay to come see our San Mateo group there. Through the years we had some unforgettable nights. It's usually clear and transparency can be quite good. The Milky Way can be seen amazingly to the south. I wouldn't be surprised if it was the best Bortle 6 zone in the U.S.