A little more than a century ago, the only way to get between the Land of Israel's more isolated settlements was to hoof it. While highways have replaced all these routes, some of them survive as picturesque paths into the past.
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One such gem is Wadi Rosh Pina, which runs from the village's original quarters up to Safed. Along the way one can enjoy stunning views of the old part of town as well as its environs, providing the best that the Galilee's nature has to provide. You'll see orchards, almond trees, fig trees, olive trees, pomegranate trees, Judas trees and berry bushes. Many of these trees were planted by the Arab residents of Jauna, a village that was the inspiration for the name of Gai Oni - the original Jewish settlement founded by Safed yeshiva bochers seeking to support themselves as farmers, in 1878, four years before the founding of Rosh Pina.
One can reach the path starting in Rosh Pina by starting at the bend in the "old" highway (8900) to Safed by a small convenience shop. Rather than taking the curve, walk straight up to a road that still shows some of its cobblestone origins. The first home on the left is "Beit Keller," built by Aharon Jeremiah Keller, one of the three founders of Gai Oni who remained in the village after a group of Romanians arrived and renamed it Rosh Pinna. It is still owned by the Keller family today. (Full disclosure: he was my great-grandfather).
Keller and the other founders bought the land from the residents of Jauna, and he lived with the sheikh until the home still standing (albeit much smaller originally) was complete. You can see images of the old settlement in the local museum. The residents of Jauna fled in during the War of Independence in 1948.
Take the path straight up along the old cemetery facing the old part of town, separated by the wadi. The street eventually turns into a gravel path that leads between the trees. On the left side, you'll walk past three springs – Ein Kadan, Ein Pina and Ein Oni. Once upon a time they had more Arabic names. Eventually Mekorot, the water company, took control and covered the sources of the springs to protect them from Bedouin, who also wanted the water.
Like so many other places in Israel, Wadi Rosh Pinna comes with its own story. When the Romanians scouted out the place around 1881-2, it was a particularly wet winter, and the wadi was fuller than normal. The scout sent reports of a river back to the homeland. In those days before Snopes, the legend grew until the people in Romania heard of a raging river. They even had one of the eventual settlers learn the craft of making boats.
When they arrived they were disappointed to see a trickling brook, but the settler's boatmaking skills came in handy. When they built the main synagogue, which can be seen from the wadi, he built a domed roof on top, which is basically the hull of a boat turned upside down.
The pastoral stroll will land you about two hours later on the eastern edge of Safed, in the Canaan neighborhood.