Contemplative practice in Judaism has taken a variety of forms, and bears a variety of names, but it's been a part of Judaism for a very long time. ("Contemplative practice" is an umbrella term which covers a variety of practices; meditation is one of those practices.) Let's start here: maybe you know that traditional Jewish practice includes praying three times a day. The traditional explanation for that thrice-daily prayer regimen teaches either that we do this in remembrance of the offerings at the Temple of old, or that we do this in remembrance of the patriarchs (or both.)
We read in Torah that Abraham connected with God in the morning, Isaac in the afternoon, and Jacob in the evening, so we do the same. And in Torah, what form did that connection take? In Genesis 24:63, when Isaac went out לָשׂוּחַ / la'suach in the fields, what exactly was going on? According to the classical JPS translation, that verb means "to meditate." So one could make the case that from the patriarchs on, Jewish prayer has always had a meditative component.
Later, during the time of the Tanna'im (the 1st and 2nd centuries of the Common Era), Jewish mystics sought to elevate their souls by meditating on the chariot visions of Ezekiel. This became a whole school of contemplative practices known as merkavah mysticism. Some of their practices were re-imagined and re-interpreted by later mystical and contemplative movements in Jewish tradition.
Meanwhile, the sages of our tradition were discussing the proper balance of keva (fixed form) and kavanah (intention or meditative focus) in Jewish prayer. Some went so far as to argue that prayer without the right meditative intention doesn't actually count. In the days of the Tanna'im, communal prayer frequently took the form of variations on known themes, where a skilled prayer-leader would improvise new words on the existing themes of the prayers. Over time, those improvised words were written down, and by the Middle Ages became fixed in more-or-less the forms we know today.
Kabbalah (the branch of the mystical tradition which began around the 11th century) features all kinds of contemplative / meditative practices. These included visualization practices (imagining Hebrew letters and focusing on Divine Names), letter combination practices (mentally combining and recombining Hebrew letters in order to elevate the mind to a higher plane of consciousness), and practices of contemplating different sefirot (aspects or facets of God) -- all of which had the goal, in one way or another, of uniting one's soul with God in a state of devekut, "cleaving" or union. (This was the subject of my undergraduate thesis, so I can go on about it at some length. I'll spare y'all the long version, though if this is interesting to you, let's have coffee sometime!)
There's a teaching in the Gemara about the Hasidim rishonim, the first generation of pious Jews, who before sitting down to pray the morning service would first meditate for an hour in order to be able to bring full concentration and intention to reciting the prayers' words -- and after the morning service, would meditate for an hour in order to let the prayers fully percolate into their hearts and souls. Two hours of contemplative practice for every one hour of liturgical prayer: holy wow!
Much later in our history, the movement we now call Hasidism, which began with the Baal Shem Tov in the 18th century, inherited those meditative practices along with the kabbalistic aspiration of seeking devekut with God. A variety of contemplative practices arose in Hasidic communities. One is hitbonenut, "contemplation." In some Hasidic schools this term connotes intellectual contemplation of divinity -- particularly in Chabad, the branch of Hasidism whose name is an acronym for three divine modes of knowing (chochmah, binah, and da'at -- wisdom, understanding, and insight.)
Another form of Hasidic contemplative practice is hitbodedut, which means "self-seclusion" -- for instance, walking alone in the woods and communing with God. This was the practice of the Hasidic master known as Reb Nachman of Bratzlav. He frequently engaged in what we would call "walking meditation," walking alone in nature, while speaking aloud with God along the way. Here's a tiny taste of a prayer attributed to Reb Nachman:
How wonderful it would be if we were worthy of hearing the song of the grass!
Every blade of grass sings a pure song to God, expecting nothing in return.
It is wonderful to hear its song and to worship God in its midst!
(That prayer can be found in A Hidden Light: Stories and Teachings of Early HaBad and Bratzlav Hasidism, by Rabbi Zalman Schachter-Shalomi and Netanel Miles-Yepez.) This form of contemplative practice tends to be fairly solitary, spontaneous, and unstructured; its goal is to establish a close relationship with God.
In the Mussar (ethical self-improvement) school which developed in 19th-century Europe, contemplative practices were refined and reframed in yet another way. One Mussar meditative practice features focusing on different middot, character-traits or qualities which we can seek to cultivate in ourselves. (These include qualities like patience, lovingkindness, order, humility, and so on.) There are visualization-based Mussar meditative practices, too. Many contemporary Mussar teachers advocate taking time each day to sit in silence and simply notice how one’s mind wanders.
All of this may sound unusual to those of us who are most familiar with the Jewish practice of liturgical prayer, known in Hebrew as tefilah. We may have the notion that meditation is something Buddhists do on their cushions, whereas Jews engage in something different altogether! Except... I'm not so sure it's all that different. I think there's a clue to the meditative quality of Jewish worship in the very word we most frequently use to mean prayer.
The Hebrew word tefilah comes from the root l'hitpallel, "to judge oneself." The fact that we use the word tefilah to mean "prayer" hints that our liturgical prayer has at least two purposes. One purpose is to help us connect with God (whatever we understand that term to mean); the other purpose is to take a long deep look inside ourselves, to see who we most truly are, to become aware of our consciousness and our thought processes, and to guide ourselves toward becoming the people we most intend to be. Tefilah is meant to connect us both outwards / upwards / God-wards -- and inwards / downwards / into our deepest selves. Both of those directions can involve contemplative practice.
As I've grown more familiar with our (occasionally wordy) liturgy, I've come to love the idea that even our wordiest liturgical prayer can be understood as a contemplative practice. Of course, in order to be able to experience rapidfire Hebrew prayer as a contemplative practice, one needs to know the words so well that they become transparent and flow from one's lips without effort -- which can be a tall order for most contemporary Jews, for whom the Hebrew may be challenging and the siddur's ancient metaphors distancing. Many of us who are not able to reach meditative states through speedy recitation of Hebrew prayers choose instead to daven shorter versions of the prayers, bringing greater intention and attention to each word.
If you've ever seen a page in a prayerbook dedicated to an image made out of Hebrew letters and words -- perhaps an archway, perhaps a menorah, perhaps a tree -- that's another very old Jewish meditative practice. It's called a shviti, after the verse shviti Adonai k'negdi tamid, "I keep God before me always" (Psalm 16:8.) The idea is to gaze at the words which make up the image and to contemplate the words and the letters as a way of keeping God foremost in one's consciousness. (I've written about shvitis before.) Some people carry a shviti with them on a keychain or on a wallet-sized piece of art, in order to be reminded of God's presence every where they go.
Some forms of Jewish contemplative practice borrow concepts and terminology from Western mindfulness practices which may be familiar to other practitioners of meditation -- such as "following the breath," "exhaling the tension from your body," "noticing how the mind wanders." Others are explicitly Jewish in origin and terminology. For example, letter-meditations featuring the four-letter Name of God, where one inhales on the י, exhales on the ה, inhales on the ו, exhales on the second ה. (That's a breathing meditation which allows every pair of breaths to be a recitation of the divine name.) Or the shviti visualization meditation I mentioned a moment ago. There are also embodied Jewish meditation practices which map the sefirot (the diagram of divine qualities, usually conceptualized as a sort of tree) onto the human body and direct energy and attention from one to the next.
At my shul, Jewish contemplative practice takes three different forms. At our Friday morning meditation minyan, we spend half an hour consciously entering into Jewish meditation practices. We follow our breath as it comes and goes, rises and falls; we notice our thoughts as they arise, and without judgement let them drift away; and then depending on the teaching I offer midway through the session, we either engage in guided meditation, or contemplate a quality we wish to cultivate, or reflect on the week now ending in order to process its ups and downs and let it go before Shabbat. That's one way we engage in Jewish contemplative practice.
A few times a year, I lead an explicitly contemplative Shabbat morning service. That's a service which takes the form of chant interspersed with silence. We don't skip any prayers or any of the elements of prayer which are required in order for a person to be yotzei (to have fulfilled the obligation of davening), but instead of reciting each prayer in full-text form, we chant only one or two lines of each, over and over, allowing the meaning of the words to soak in to our hearts and souls. Then we sit in silence for a few moments as the prayer's meaning continues to resonate and reverberate in us before we move on to the next chant. That's a second way we engage in Jewish contemplative practice.
And the third form happens frequently during the Shabbat morning services I lead, the "regular" ones which aren't explicitly contemplative. Every time we reach a kaddish, and I remind us that the kaddish is a doorway in the service from one part of the service to the next, and invite us to pause for a moment, and take a deep breath, and see what we're feeling in that moment, and then to carry that feeling (whatever it may be) into the next part of our prayers? That's a Jewish contemplative practice, right there, and that's a third way that we can enter into this ancient tradition.
Jewish contemplative practice can take the form of Torah study, chanting, sitting in meditation (not necessarily in "lotus position" or sitting on meditation cushions -- you can meditate sitting comfortably in a regular chair if that's what works for you), walking in nature, gazing at names of God (on the printed page or in one's imagination), focusing on personal qualities we want to cultivate, reciting the prayers in our siddur with deep intention and attention...and more. Many of these meditative practices are as old as our prayers. And all of them have deep roots in classical Jewish tradition.
If this is interesting to you, don't miss Rabbi Jeff Roth's Jewish Meditation Practices for Everyday Life: Awakening Your Heart, Connecting With God. He's the founder of the Awakened Heart Project, which has as its mission "to promote the use of Jewish contemplative techniques that foster the development of a heart of wisdom and compassion." Rabbi Roth's focus, both in the book and in his organization, is bringing meaningful spiritual practice to life.
For a different perspective, I also recommend Rabbi Aryeh Kaplan's Jewish Meditation: A Practical Guide. Rabbi Kaplan is an Orthodox rabbi, and his book explores the deep history of Jewish meditation as well as offering "a guide to a variety of meditative techniques: mantra meditation (with suggested phrases and Bible verses to use as mantras); contemplation; visualization; experiencing nothingness (which he does not recommend for beginners); conversing with God; and prayer." (That's from the Amazon description.)
If you're in or near the Boston area, you might want to check out Nishmat Hayyim (Breath of Life): the Jewish Meditation collaborative based in Boston.
Rabbi Sheila Weinberg, author of Surprisingly Happy: An Atypical Religious Memoir, is also a good resource for Jewish contemplative practices. You can listen to a podcast of some of her teachings here at the Awakened Heart Project. Speaking of which, there's wonderful series of podcasts at the Institute for Jewish Spirituality, by Rabbi Sheila Weinberg and many others, which draw on Jewish contemplative practice(s).
(I welcome suggestions of other resources in comments!)