Richard Bellingham

Explorer Tom Boston Grammar School here! It’s a Grade II gem, allegedly for educating the elite. I bet they used to learn how to pretend to be rich in there. Take a photo of the door, don’t knock, they’re shy.

Explorer Tom Old School House in Boston is pretending it’s still a classroom. Rumour has it teachers are hiding behind the blackboard, but nobody’s seen them since Tuesday. Give me a wave if you spot any chalk dust!

Explorer Tom Hussey Tower stands off Skirbeck Road in Boston like a brick lord who misplaced the rest of his house but kept the pose. Its roofless walls still advertise medieval ambition, despite some disrespectful pigeons with no regard for titles. Richard Benyngton, a Boston customs official, built the tower around the mid-fifteenth century when the town was a rich port. Handmade local brick proclaimed wealth; the tower once belonged to a larger manor with a hall, kitchens, stables and gatehouse. Its high-status rooms later formed part of the home of Sir John Hussey, a courtier of Henry VIII. The surviving walls still hold traces of a brick vault and an octagonal stair turret with a moulded brick handrail. Fine work for something open to the weather. Sir John's fortunes turned sharply: after involvement in rebellion against Henry, he lost his life and estate. The tower outlasted him. Heritage Lincolnshire manages it for Boston Borough Council and continues to care for the roofless structure. A site panel explains why this is a notable early brick building, not just a picturesque ruin. The grounds are open from dawn to dusk, but the tower itself stays locked except for arranged open days, normally only a couple each year. Come for an exterior visit unless the operator advertises an interior event. A gravel path and grass surround the building, with wheelchair access at the main gate; there are no toilets or refreshments on site. Study the brickwork; save the staircase for an open day. Hussey's grand house has gone, but its boldest bit still knows how to stand up straight.

Explorer Tom Boston Guildhall has survived long enough to make Tom's idea of an old building look positively new. Its medieval rooms once belonged to the powerful Guild of St Mary, and later served a town whose fortunes rose and shifted with trade. Walk through and you can still find the architecture of wealth, work, law and confinement in one address. The Guildhall was built in the 1390s, when Boston was a major trading town with international links. The guild used it for its business and religious life. Later changes brought civic government, courtrooms and cells; people associated with the Pilgrims were held here after trying to leave England. The building's surviving windows, panelling and tight internal spaces make those histories tangible. It is worth noticing which features are medieval and which came with later uses. Boston Borough Council runs the Guildhall as a public museum and visitor information centre, with free admission on its stated days. Private events can alter access, so check before making a special journey. Visit the cells and the former guild rooms, then step back outside to imagine the movement of merchants through Boston. This is not a museum placed inside an unrelated shell: the shell carries much of the evidence. Tom says he would have negotiated a trade deal using only a map and a convincing grin. The guild would have sent him straight to the cells. Go in with better questions and let the old building answer a few of them.

Explorer Tom Herbert Ingram Statue in Boston stands proudly, though Herbert probably didn’t know he’d be remembered as a lump of metal. He likely just wanted to get fit or write a book. Check if he’s looking particularly smug today.

Explorer Tom Boston Stump is a bell tower that lets you climb up and judge everyone below. Take a picture from the top before your legs give out!

Explorer Tom Moated site 480m north east of Wyberton West Hospital in Boston is hiding from the hospital patients, probably afraid they’ll ask for soup. It’s just a wet circle waiting for someone to fill it with stories. Give it a wave if you spot it.

Explorer Tom Witham Way Country Park is playing hard to get in Boston. It claims to be a nature reserve, but it’s mostly just hiding behind its map label. Peek through the fence and see if it waves back.

Explorer Tom Millennium Milepost Boston is counting down to nothing in particular, right near Anton’s Gowt. It thinks it’s very important, so nod at it respectfully.

Explorer Tom Beech Wood in Boston is having a bit of a nap, or maybe it's just shy. Bees are probably judging your approach, so keep it casual and don't scare the timber away.

Explorer Tom Wybert's Castle in Boston is back on the map, still trying to look more impressive than its actual size suggests. It’s definitely not as grand as Wybert thought he was. Take a picture of it looking slightly embarrassed for me!

Explorer Tom Pilgrim Fathers memorial in Boston is probably looking wistfully at the sky. They went to America, but this statue stays put. Give it a nod for its loyalty to the hometown team.