Shepherd started his career at Falkirk, making his debut as a 17-year-old in August 2013 when he came off the bench to score the winner for the Bairns in a 2-1 Challenge Cup win against Ayr United at Somerset Park.
He made 64 appearances for Falkirk over five seasons at the club, where his time also included loan spells at Stirling Albion, Brechin City and Edinburgh City before making the move permanently to the Edinburgh side for the start of the 2018-19 season.
Shepherd hit 23 goals in 98 appearances for The Citizens before signing for Forfar Athletic, where he has spent the past two seasons. He made his debut in sky blue colours in a League Cup match against Hibernian and went on to make 71 appearances.
He scored eight goals, which included a brace in a narrow win over Stranraer in January of this year.
His appearances, said the Forfar website, were “always full of energy and hard work”.
Bayview boss Crawford said: “I’m delighted to bring Scotty to the club. I first worked with him when he was 15 at Falkirk and have kept an eye on his progress since then.
"He’s at a good age, 25 (26 at the end of this month), with the best years ahead of him.
"He’s quick and already has good experience in both Leagues 1 and 2 which will help us with the challenges we will face this season.”
Shepherd, who will join up with the squad when they return for pre-season in June, added: “I worked with Stevie Crawford at Falkirk when I became full time and have kept in touch with him over the years. I know what a great coach he is and I think he will bring out the best in me. I am delighted to come on board at East Fife and can’t wait to get started.”