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Documented deeds for the Chequers Inn site go back to 1695, concerning a transaction between Eleanor Pierce and John Gyer for a 999-year lease.

The chequered sign, originally hanging from the roofs eaves represents probably the oldest in the world; a chequered sign was discovered during the excavations of the ruins at Pompeii. In early times it denoted houses where money transactions were carried out – and the local sign is likely to derive from the fact that the Salt Exchequer Offices for the local salterns had their headquarters at Lower Woodside Green.

Lymington has a centuries old history in salt making, dating back from late Saxon times. It fell in decline in the early years of the 19th century due to the burden of taxes on salt and coal, and hastened by the opening of rock salt mines in Cheshire which could be brought down by the railways. Technological improvements introduced in the production of salt from brine enabled production to be continued throughout the year so weather ceased to be a factor.

The Chequers Inn is situated next to the salterns where the shallow pans specially constructed along the estuaries and marshes, can still be seen. Two boiling houses survive though their role has changed, but there is little else to show of an industry that had once been of major economic importance for the people of Lymington and the surrounding area.