You can’t add your own fonts in manually. Try checking for a similar one on the Appearance → Custom Design → Fonts page. Or, if you can’t find the font you want there but you can find it at Typekit.com, then you can purchase a Typekit plan and use the advanced mode for fonts to add in any of the fonts in the Typekit library.
The Headings option on the Appearance → Custom Design → Fonts page will also affect widget headings.
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