Virginia is the ideal stop for traditional classroom supplies, which are tax-free up to $20 per item during a three-day tax holiday weekend. The district is sandwiched directly between Virginia and Maryland, which both offer tax-free shopping windows in August. Related articleAs Virginia's tax-free window closes, Maryland's week-long "Shop Maryland Tax-Free Week" opens, running from August 9–15. Maryland offers a much longer window to buy apparel and footwear priced at $100 or less per item tax-free. School supplies surgeBig picture view:Families are expected to spend nearly $175 on school supplies this year, according to data from Groundwork Collaborative.