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With Macports, I realize that there are ports gnupg and a newer gnupg2. I'd like to use GnuPG to encrypt files. Should I install both, or just one is enough? If I installed both, are both compatible with each other? Does it matter which one I install first matter at all?

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GnuPG 1

GnuPG 1.4 ("classic") will stay for embedded and server usage, as it brings less dependencies and smaller binaries. Earlier, it was often installed as gpg, today it is more often named gpg1 (depending on distribution).

From the GnuPG 1.4 man page:

This is the standalone version of gpg. For desktop use you should consider using gpg2 from the GnuPG-2 package (On some platforms gpg2 is installed under the name gpg)

GnuPG 2

GnuPG 2.0 is a redesigned version of GnuPG -- but changes are mostly on internal level. The newer version is split into multiple modules, for example there are also modules for X.509 (used by S/MIME).

From man gpg2:

In contrast to the standalone version gpg, which is more suited for server and embedded platforms, this version is commonly installed under the name gpg2 and more targeted to the desktop as it requires several other modules to be installed.

GnuPG 2.1

An important change came with GnuPG 2.1, which combines the formerly separated public and private keyrings (pubring.gpg vs. secring.gpg) into the public keyring. This has been implemented in a manner keeping things compatible, so you can still use GnuPG 1 when GnuPG 2.1 integrated the private keyring, but changes to the private keys will not show up for the respective other implementation. From the changelog:

[...] allows co-existence of older GnuPG versions with GnuPG 2.1. However, any change to the private keys using the new gpg will not show up when using pre-2.1 versions of GnuPG and vice versa.

To directly answer your question:

Should I install both, or just one is enough? Does it matter which one I install first matter at all?

Just install both. They don't interfere anyway. Install gpg (if not installed anyway) for other applications that access it (like package managers, mail clients, ...), and gpg2 for "direct use" on the command line.

If I installed both, are both compatible with each other?

Both implement the OpenPGP protocol, so they're compatible to each other regarding data shared among them. Additionally, they're (mostly) using the same commands and options, so most of the time you could switch between them arbitrarily.

GnuPG 2.1 makes changes to the private keyring invisible to pre-GnuPG 2.1 implementations (see above in the GnuPG 2.1 section).

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    gpg2 doesn't seem to see the private keys that gpg sees. For instance, gpg2 --list-secret-keys gives no output, but gpg --list-secret-keys does give output.
    – Flimm
    Commented Jul 23, 2016 at 10:15
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    This is exactly what I described with the important difference between GnuPG 2 and 2.1: GnuPG 2.1 stores private keys in another file. Your private keys are stored in GnuPG 1.4's secring.gpg, which is not queried by GnuPG 2.1. Copy them to GnuPG 2.1 through gpg --export-secret-keys [key-id] | gpg2 --import.
    – Jens Erat
    Commented Jul 23, 2016 at 10:22
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    gpg2 actually automatically imported the gpg keys for me (cygwin)
    – lucidbrot
    Commented Nov 6, 2017 at 15:36
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    This answer may be a little out of date. On Ubuntu 18.04 bionic the gpgv1 package is described as "deprecated "classic" version" and gpgv2 is described as "dummy transitional package." Installing the plain gpg package gives gpg version 2.2.4. So it appears that gpgv1 is going away and gpgv2 (referred to simply as "gpg") is the new standard.
    – Mark Doliner
    Commented Feb 7, 2019 at 22:10
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    I don't know how much this changes things, but there is some confusion here: gpgv is not the same as gpg. On Debian the gpgv package says: "gpgv is actually a stripped-down version of gpg which is only able to check signatures. It is somewhat smaller than the fully-blown gpg and uses a different (and simpler) way to check that the public keys used to make the signature are valid. There are no configuration files and only a few options are implemented.". The package names for the actual gpg are gnupg and gnupg1. To me that doesn't say v1 is going away, only that v2 is the standard.
    – FrontierPsycho
    Commented Sep 15, 2022 at 15:15

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