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Stargaze on a dry, clear night. Stargaze in the summertime. Get out of the city for the most relaxation. Watch out for wildlife.
This way, you'll see more stars, and you won't get wet from rain, or overly-hot due to humidity. A breeze can mean less pollution near a city, but strong wind can be chilly, so bring extra blankets and sweaters if it seems windy. Summer nights (during June, July, and August) can offer great stargazing conditions. You'll also be more comfortable than you would be in the winter, and can pack a bit lighter. You are most likely to see meteor showers in the summertime. The "Perseids" meteor shower is awe-inspiring, and visible from nearly everywhere in the Northern Hemisphere. It occurs every August. Some constellations that can be seen year-round (meaning they are "circumpolar") are: Cassiopeia, Ursa Major, and Cepheus. Try to avoid major cities and densely populated areas. Stargazing will be difficult in these areas because of the light pollution and noise they produce. For a relaxed stargazing experience, you'll want to find some peace and quiet, likely in a more rural area. If you are able to find a sparsely populated, rural area to stargaze in, chances are good that some wildlife will be around. Deer, bears, coyotes, raccoons, and possums are common camp-crashers. Research what animals are found in your area, and keep a sharp eye out while you are outside at night. Wherever you decide to stargaze, always bring bug spray. You certainly won't be comfortable if you're swatting at mosquitos all night! You can bring a bright floodlight or something to make loud noises with, to deter animals that may come near while you are stargazing.