Looking at starter ventures, a few places to visit and further adventures for Book 2 of Steam Highwayman.
Highways and Holloways
Steam Highwayman is the 100 Endings Book Club read for May 2026. There is a guide for book 1, but in this series you can start in any book. And book 2 is actually a better starting point.
The second book of the Steam Highwayman series, Highways and Holloways continues and expands on the content from the first book. It's a far more polished book with more content and more opportunities. There's many places to ambush people, more guild politics, an airfield with flights abroad, a sky pirate and a few set pieces.
The same general advice also applies from the Book 1 Guide (find somewhere to store things, prioritise bonuses to Nimbleness, visit the pubs for opportunities)
There are six starting characters, each with a different high ability of 6. Of these it's worth noting the revolutionary starts as a member of the Compact for Workers' Equality, the character from poverty has a Nimbleness of 6, and the noble has a Letter of Introduction.
5 Starting Venture in Highways & Holloways
Like most open-world series, getting started can take a while in Steam Highwayman. It's easier to find jobs or good ambush spots in H&H than in book 1, but here are 5 ventures looking into to begin.
- Helping out Mr Sands, a gamekeeper who can be found in the Red Lion at Woodcote. You'll need to help out in the woods, but you'll get a useful friend and told the secret of dead weasels.
- The Angel in Henley lets you watch passing traffic. From there you can watch and choose targets to rob. You'll need to be a competent highwayman, but some of them are worth the effort.
- Seeking the right punchcards for J. Fox & Son in the Industrial district of Reading. Finding the right set(try the attic of a grand house near Stonor) opens up a whole other part of the gamebooks. The secret of using (and even making) punchcards for yourself.
- Helping out the Station-Master of Henley Railway Station. You'll need to observe telegraph stations (marked on the map) or steal from the Telegraph Guild. But the station master will pay you well for each codebook you find / make, and the Telegraph Guild has other enemies (such as the Coal Board).
- Revealing a fraud to Lord Brigg, who can be found south of Aston. You'll need to go to the Flower Pot in Aston, then approach Lord Brigg with a letter of introduction (and some ING or GAL). But the payoff is worth it, giving cash, a place to stay, a new skill, a good friend with nobility and a decent croquet partner.
5 Places to Visit in Highways & Holloways
There are a few places to note, outside of the main settlements of Henley, Oxford, Reading and Wallingford.
- The village of Bix is northwest of Henley, with a workshop for your velosteam and a tollman worth talking to. There's a decent ambush point (on way to Nettlebed) but the highlight is the church. Father Patrick offers up a unique quest or a robbing opportunity, plus some other ways to be helpful in the future.
- Elvendon Priory has a fair amount going on. There's healing, an opportunity for some robbery, and three different ways to help out. None of these are easy, but two end in possible stat advancements and one can lead to the most unique ending in Steam Highwayman! Also checkout nearby Goring, as it's got lots going on too.
- Stokenchurch in the northeast is the largest town without a Constabulary checkpoint. It also has a decent market, an inn with a room to stay in and the Coal Board, who offer doctor and some work. Appropriately there's also a church with some cash if you're in need.
- The village of Turville (between Stokenchurch and Henley) is small but has two extremely important finds. One is a forge with velosteam repair, velosteam customisations and a way to get a large Nimbleness boost. The second is morris dancers, the importance of which needs no explaining. Nearby is the village of Fingest which is worth wondering around. And heading north from Fingest you can find a mill with someone in need.
- The Valentine Woods have a place to set up a hide-out, if you bring an axe and tarpaulin. While not exciting, it's a constable-free place to safely stash goods. It's also a place to flee to if you're dying! Easiest entry point is from Stoke Row.
5 Further Adventures in Highways and Holloways
Once you're up and running, there's a few longer threads you can follow in Highways and Holloways. All without leaving the book.
- Captain Coke is an airship pirate. He's wanted (check out the Angel in Henley) with a big reward on his head. Butthere are ways to befriend him, and to his friends he gives a place to stay, access to supplies and a place to rest. And he can help you out with any loot that's too bulky for you to carry away yourself. You'll want decent Nimbleness before taking on the Coke challenge though!
- The Croquet Game at Fawley Court (NW of Henley) is a big set piece with a variety of outcomes. You can choose from 4 different partners and repeat it. You'll need a Letter of Introduction or the right contacts to get a game.
- Get involved in Guild Troubles. The Coal Board, Telegraph Guild and Railway Master in particular in H&H. With chances to rob, compromise, blow up and burn down a variety of places. There's also work for the Compact (there's a route to joining by being captured by the Constables) and bit for the Haulage guild if you have a medallion from another book.
- The Rotherfield Greys Airfield west of Henley properly opens up the world. With the right skills or opportunities you could be off on airship trips to Belize, Iceland, Budapest, Cairo or nearer to hand. Each trip is unique with it's own opportunities and rewards.
- Getting a boat and Steaming the Thames. You can get one in Reading and there's a fair amount of river to explore. You can actually make good money doing it too if you want an alternative income. Or theirs river pirates, jousts, barge feesm narrowboats and a race to enjoy. Make sure to go visit Oxford. If you've got books 1 and 3 you can also take boat and cargo down to London.
Finishing Up
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