Dan, the facilities manager at a small Massachusetts college, discovers a time machine, and when he tries it out, he finds himself transported to the year 1700. Dan tries to get help from a scientist named Chris.
Dan and Deb travel to an ancient era to rescue Chris, but they find themselves on an adventure during the Great American Revolution.
Deborah contemplates her relationship with Dan after discovering that he may not be such an amazing inventor as he claims to be.
The trio travels back in time to the 1990s so Dan can achieve his earliest goal of completing the famous ice cream sundae at a local parlor.
The trio encounters Al Capone while attempting to cash in on the 1919 Chicago World Series in order for Deborah to purchase her own ice cream parlor.
Deb and Chris become friends with Al Capone to retrieve their time travel luggage, but Dan wants to remain cautious.
Chris seeks assistance from John Hancock and Sam Adams when Deb realizes her desire to reopen Chadwick's ice cream parlor.
John Hancock and Sam Adams compete in a battle to see who gets to attract the woman.
Dan's attempt to reclaim Chris's job fails after Dr. Cobell has a sudden heart attack.