| Name | Category | Address | Opening times |
|---|---|---|---|
| Bisca | Stair contractor | Bisca House, Sawmill Ln | Mon–Thu 08:00–17:00 |
| Bridge Street Fisheries - Fish & Chips | Fish and chips takeaway | 6 Bridge St | Daily 11:30–16:00 |
| Helmsley Brewing Company | Brewery | 18 Bridge St | Mon–Thu 12:00–21:00 |
| Helmsley Castle | Castle | Castlegate | Daily 10:00–17:00 |
| Helmsley Open Air Swimming Pool | Swimming pool | Baxton's Sprunt, Helmsley | Thu 11:00–19:00 |
| Helmsley Traditional Sweet Shop | Sweet shop | 1 Barkers Yard | Daily 10:00–17:00 |
| Helmsley Walled Garden | Garden | Cleveland Way, Helmsley | Wed–Sun 10:00–16:00 |
| Peter Silk of Helmsley | Interior designer | 10 Castlegate | Mon–Sat 10:30–16:30 |
| The Feather Trail Cafe | Cafe | 3 Castlegate | Mon–Tue 09:30–16:00 |
| Nationwide Building Society | Building society | 2 Bridge St | Mon–Thu 10:00–15:00 |
| All Saints' Church, Helmsley | Church of england church | Church St | Mon–Sat 09:00–17:00 |
| Carter's Countrywear | Clothing shop | 7 Market Pl | Mon–Sat 09:30–17:30 |
| North Yorkshire Cottage Holidays LTD | Holiday home letting agency | 3, Meeting House Court | Mon–Tue 10:00–15:00 |
| The Bike Doctor | Bicycle repair shop | Unit 4, Helmsley Walled Garden | Mon–Tue 07:00–19:00 |
| Coopers of Helmsley | Modern British restaurant | 8 Bridge St | — |
| Duncombe Sawmill LTD | Timber merchant | Sawmill Ln | — |
| Helmsley Wines | Wine shop | 4 Bridge St | — |