Short answer: The ferries are the entertainment here — cheap, short and endlessly interesting to a two-year-old. Blackpool Sands is the family beach but it is fine shingle, not sand, so warn toddlers before you arrive. The Sail Loft and the Royal Castle both have room.
Dartmouth's great advantage with a toddler is that the entertainment is free, frequent and short. Ferries run across to Kingswear and down to the castle, they take a few minutes, and to a two-year-old a boat is a boat. The quay is level, the Embankment is level, and you can spend a morning watching things move without spending anything much.
Blackpool Sands is the family beach fifteen minutes west, and it is very good — sheltered, blue flag, lifeguards, a café, showers, kayak hire and a boardwalk running down towards the water. But it is fine shingle rather than sand, and one reviewer puts it perfectly: toddlers will need fair warning to prevent any meltdowns.
Bring beach shoes and set expectations before you arrive. Sandcastles are not happening. Pebble sorting, on the other hand, is a perfectly good toddler activity.
The quay, the Embankment and the flat streets immediately behind them. The streets climbing away from the water get steep quickly, and Bespoke — the best coffee in Dartmouth — is explicitly described by reviewers as unsuitable for pushchairs or walking frames.
Worth stating plainly. Dartmouth Castle has a great many steps and reviewers are clear it is not suitable for pushchairs. You can still take the ferry out, enjoy the approach and the tea room, and treat the fort as something to look at.
Woodlands Family Theme Park, twenty minutes away near Totnes, has large indoor play areas. Totnes itself has the Rare Breeds Farm — reached through the steam railway station, wheelchair accessible, and you can feed most of the animals for a pound a bag, which is close to ideal at this age.
Time the beach around a falling tide. Firm wet sand is far easier to push a buggy across than soft dry sand, and shallow pools left behind by the receding water are safer and warmer than the sea itself.
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