The best family-friendly hikes and walks around Weymouth

The Smugglers Inn is a historic, 13th-century thatched country pub and boutique hotel nestled on the clifftops of Osmington Mills, Dorset. Boasting sweeping views of the English Channel and the Isle of Portland, this Hall & Woodhouse coastal gem sits steps away from the rugged Jurassic Coast and the South West Coast Path. Steeped in local lore, the inn served as a notorious 17th-century smuggling landing site and was once the headquarters for the French smuggler Pierre Latour and the infamous Emmanuel Charles. Inside, the building retains its authentic, centuries-old character with low oak-beamed ceilings, original flagstone floors, and a historic central chimney. Today, it operates as a cozy retreat featuring eight en-suite bedrooms, EV charging bays, and a large tiered outdoor terrace complete with a natural stream. The restaurant serves seasonal British pub classics, hearty Sunday roasts, and locally brewed Badger Beers. Known for its warm hospitality, the inn remains highly popular with hikers, families, and dog owners looking for a scenic countryside escape.

Cut right into the limestone of Osmington Hill, the Osmington White Horse is a massive, 280-foot-long hill figure that has been watching over the Dorset coast since 1808. Unlike most chalk horses, this one features a rider: King George III on his favorite charger, Adonis. The King loved vacationing in nearby Weymouth, so local residents carved it to honor him. However, local legend says the design backfired. Because the horse is depicted riding away from the town, the King supposedly took it as a passive-aggressive hint that he wasn't welcome and never came back. Over the years, it has been a target for playful pranks—even getting a temporary plastic unicorn horn in 2011. It is a fantastic landmark to spot while driving along the A353 road or while enjoying a breezy hike on East Hill.

St Osmund’s Church in Osmington, Dorset, is a historic parish church with origins dating back to around 1170. Dedicated to the 11th-century Bishop of Salisbury, the building forms part of the scenic Ridgeway circuit. While extensively rebuilt between 1845 and 1846 using local stone and Ham Hill dressings, it beautifully incorporates its medieval heritage. Surviving architectural treasures include a Romanesque chancel arch from circa 1200, a restored font of the same era, and a 14th-century north arcade. Its striking two-stage west tower houses four historic bells, including one dating back to the late 14th century. The churchyard features two Grade II listed monuments, including a 1678 table tomb. Famed landscape artist John Constable even captured the church during his 1816 honeymoon in the village, cementing its place in English cultural and architectural history

The Springhead is a traditional country pub nestled in Sutton Poyntz near Osmington. It features a large orchard beer garden with scenic views of the Osmington White Horse. Known for its Sunday carvery, log fires, and wood-fired pizzas, this dog-friendly retreat is perfect for walkers exploring the Jurassic Coast.

The only white horse to have a rider. It is George III, on top of his horse Adonis.

Very nice picnic spot with toilets. Not a big detour.

part of the 17 miles of earthworks.

The Oasis Café is your ultimate beachfront "pit stop" at Preston Beach. Forget fancy—think hearty breakfasts, fresh crab sandwiches, and epic views of the Jurassic Coast. It’s the perfect place to watch the waves crash while you tackle a massive slice of cake. Sandy paws and salty hair are definitely welcome!