Christopher McKenzie, 34, pleaded not guilty in Windham Superior Court Criminal Division to two felony counts of larceny from a person.
He remained jailed in lieu of $10,000 bail.
Brattleboro police said they received a report Thursday evening that a man had approached a woman in the downtown area and demanded money.
She sprayed him with mace, and he fled, police said.
Later, two people reported that they had been robbed at about 2:45 a.m. as they walked on Frost Street.
The suspect displayed a knife, and both victims handed him their wallets, police said.
McKenzie was arrested a short time later as he walked in the Harmony Lot.
At his arraignment Friday afternoon, McKenzie told Judge John Wesley that he had been staying at the overflow shelter in Brattleboro.
McKenzie, who originally is from Windsor, has a criminal record that includes two felony convictions for grand larceny and burglary.
Steven Brown, Windham County deputy state's attorney, said there is a possibility that additional charges will be filed against McKenzie in connection with the Brattleboro incident.
Mike Faher can be reached at firstname.lastname@example.org or 802-254-2311,