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Old Town HERITAGE Trail - Start Here


We’re going to guide you along Scarborough’s twists and turns, exploring the history and heritage of the town.
We’ll also throw in a few folklore tales of adventurers, pirates and smugglers.

This page gives you a free preview of the full heritage trail (which can be bought in the "Purchase A Trail" pag
e). Each checkpoint has a dedicated page packed full of local information, history and heritage - you'll need to purchase the trail and sign in to view it.

When you purchase the full trail, you'll also get a map to download and follow, complete with each checkpoint, as well as sitting areas, perfect photo spots, public conveniences.

Scarborough Heritage Trail Start Here
 We begin the Heritage trail on Eastborough, the heart of Scarborough’s Old Town, and the gateway to the sea. You can start at any checkpoint as the route is a loop.
Eastborough Scarborough Old Town Heritage Trail

19 Eastborough

One of the main routes to the sea front, Eastborough remains one of the busiest streets in the town - with thousands of visitors making their way to the beach in the summer months. It has always been a prominent commercial hub.

Find out more about the history of traders and merchants in the area, as well as the doomed tram route.

CHECKPOINT 2: Merchants Row

Now walk around the corner of Leading Post Street (the cobbled street outside our building), and onto Merchants Row. You should be facing the Mariners House (now a B&B), with the 18th Century residences on your right hand side.

This little cobbled street is filled with tales of smugglers, and a ghost story that'll send shivers down your spine.
Find out more >>

West Sandgate

Walk down to the bottom of Eastborough - West Sandgate is near the bottom of the hill just before the car park.

Originally a medieval stream, and then one of the earliest settlements in the area, this little cobbled street leads to one of the oldest surviving pubs. A little further along is the Butter Cross, marking the site of a popular medieval market.

CHECKPOINT 4: Lifeboat station

Come to the end of Eastborough, and cross the traffic lights. The Lifeboat Station is just by the entrance to the beach.

  • The shipwrecks and tragedies which led to the lifeboat station

  • What brought thousands of Victorian visitors to our golden shores? 

  • The origins of other seaside traditions you may be familiar with. Fish & chips and ice cream, anyone?

  • The spooky tale of Lydia Bell's beach hauntings

The harbour

Walk past the West Pier to get to the entrance of the harbour.

  • History of the harbour

  • Maritime folklore and superstitions

  • Sea monsters, sirens, mermaids and other local nautical myths

CHECKPOINT 6: North wharf

Walk behind ASK Italian restaurant, to the harbour wall.

  • Scarborough's long history as a port town

  • Learn about the earliest fishermen

  • Fishermen folklore and superstitions

  • Long-standing Boxing Day traditions including the Fishermen vs Firemen football match

Pubs and ale

Come out onto Sandside and cross the road to the King Richard III pub

  • History of alehouses in the town

  • At one point Scarborough had over 100 pubs - find out why we had so many!

  • King Richard III - a Royal Resident

  • Lost Medieval Pubs


Further along Sandside is the old ship building yard once owned by the Tindall family

  • The rise of shipbuilding in Scarborough

  • Famous ships built or moored in Scarborough including the "First Fleet" convict transport, and a visitor favourite - The Regal Lady

  • Sea Shanties

The lighthouse

Follow Vincent's Pier down to the lighthouse

  • The history of the lighthouse and pier

  • The Diving Belle Statue

  • The ghost of Captain Appleyard

CHECKPOINT 10: The Three mariners (a smuggler's haven)

Come back onto Sandside, and turn down the little cobbled street between Casino Royale and the cafe.

At 47 Quay Street stands one of the first pubs in Scarborough, and a well known smugglers hideout

  • A smuggler's haven - the history of this medieval pub

  • Pirates, privateers, bucaneers and smugglers - what a difference a name makes!

  • A ghostly tale of a greedy Captain who still protects his loot

Dog & Duck Steps

From the old Three Mariners, walk along Quay Street until you reach a set of steep steps beside house number 38

  • A grim tale of murder and hauntings

  • The origins of the lane - who was the Dog and who was the Duck?

  • George Reader and the Evelyn & Maud Shipwreck

For an accessible alternative route to checkpoint 12 without steps, head back along the seafront back to Eastborough. The cobbles up West Sandgate lead to Castle Road, but if these are too steep, continue up Eastborough until you reach St Helen's Square (by the market). Alternatively, skip ahead to checkpoint 15 at the markethall.

CHECKPOINT 12: the castle

Walk up Dog & Duck Lane until you reach the castle footpaths - keep going until you reach the top.

  • Romans, Kings, Wars, Sieges, Iron Age Celts, Viking Raiders - the site of the castle has been at the centre of the town's history

  • Beautiful views of both bays

  • The ghosts of the castle

Anne bronte's grave & St. Mary's Church

Walk along Castle Road until you reach Anne Bronte's grave (on the other side of the wall to the car parking spaces outside the castle)

  • The oldest church in Scarborough dating back to the 1100s

  • Anne Bronte's grave (and ghost story!)

CHECKPOINT 14: Paradise

From St. Mary's Church, walk past the car park on Church Lane to Paradise

  • Stop to take in the views of South Bay

  • Learn about Paradise House - another smuggler's haven, and more recently the birth place of George Cayley and Graham Sea Training School

Market hall

Make your way down to the Market Hall on Market Way - there are several routes you can take throughout the old, winding cobbled streets.

Try walking to the end of Paradise, and down Church Stairs Street, onto St Mary's Street, then turn right onto St Sepulchre Street until you reach the back of the market. Alternatively, walking along Castle Road to Tollergate, and then onto Friargate will bring you to the same area without any steps.

  • The first purpose built market hall in the town

  • Scarborough Fair - history of street markets

  • Market Vaults - packed with independents and crafters

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