Last August, during my GenCon recap, I expressed some nostalgia for the old hex-and-counter conflict simulation wargames from Avalon Hill, SPI, and other companies that I remember seeing, but never getting a chance to play before they largely faded away. I've spent a couple days trolling through Board Game Geek and elsewhere exploring this subject, and have happened on a couple of games that I'd really like to try.
"Hammer of the Scots" (2002, Columbia Games)(img) is a block wargame that explores the Wars of Scottish Independence, which simulates a fog of war in a manner reminiscent of "Stratego". It seems to be well-regarded, covers an interesting topic, and hopefully looks enough like a Euro-style game that I may be able to rope some family into playing. Unfortunately, it's a two-player game; I suspect that part of the reason so many interesting games get played so rarely is that they're very particular about the number of people who may participate in what is an inherently social activity.
"Age of Napoleon" (2003, Mayfair Games)(video) is a grand strategy game overviewing the Napoleonic wars from 1805 to 1815, with a counters and a card-driven system to represent combat events and shifting diplomacy. It seems like a game I'd enjoy at the same level I enjoyed "Axis & Allies" back in the day, with a history theme I have a nascent and developing interest in, an interesting representation of the vagaries of diplomacy, and grand-strategy-level play light enough to play in an afternoon or evening. Sadly, it is also only a two-player game.
Battle Cry (2000, 2010, AH/WotC) spawned the Commands and Colors system that drives several popular history- and fantasy-themed strategy games. These games, like Command and Colors: Ancients (2006, GMT Games) seem to be very popular and fun, but more game-y than simulationist. I'm a little burned out on WWII and fantasy battle games, and would like a more hardcore take on ancient and American Civil War combat, but this is probably a good game to get, anyway: there's a sesquicentennial coming on, and my interest in the Civil War will likely be high for some time. A game-y system is more likely to attract players, and the 150th anniversary edition includes a lot of battles from the western front important to the Ohio River Valley (Fort Donelson, Perryville) that receive scant attention from wargames.
Entdecker: Exploring New Horizons (2001, Mayfair) is a prequel to "Settlers of Cataan" by the same designer, which uses tile placement to represent the exploration of an archipelago and create territory to be claimed by the players. My family enjoys playing Cataan and Carcassone a lot, so this game may garner some similar interest while being a nice change of pace from those games. It's also the first multiplayer game on this list. =/ There's also a bunch of children's games, like "LEGO Minotaurus", "Max", and "Blokus", that may be a worthy step up from "Candyland".
But I started all this by looking into what historical wargames people are playing these days. Going through all these games, I've started to turn against some of the games like C&C:A that make compromises with historical accuracy for better gameplay; Who wants to play a historical wargame if it doesn't accurately represent the personalities of individual Roman commanders or the interaction of rampaging elephants with pre-Marian legions at Cannae? Terribly unbalanced scenarios, stacks of chits, and endless consultation of combat results tables are a small price to pay for the historic verisimilitude only an old-school hex-and-counter game are supposed to provide!
So perhaps for ancient-era wargames something like SPQR Deluxe (1992, 2008, GMT Games)(img) might be the way to go. It covers most of the Punic Wars and several battles through the Roman Republic era. And ancient tactics are kind of interesting; the way units are laid out in lines and blocks is kind of "chess-y".
A better idea to dip toes in this water might be to try one of the old free or introductory low-complexity wargames, like "Battle for Moscow" (1986, GDW; 2009, VPG)(img) or "Napoleon at Waterloo", an introductory game put out in 1971 by SGI before it was acquired by TSR, and now freely available.. The NAW system was the basis for "Blue & Gray" (1975, SPI; DG), a relatively lightweight Civil War wargame, as well as Napoleonic games. "Battle of Honey Springs" (2007, LPD) is another free introductory print-and-play wargame that cover most important ACW battles in Indian Territory, now Oklahoma. And if ~that~ is any fun, then try to something newer like "Three Battles of Manassas", Perryville, or other series (1, 2, 3) before considering a monster game like "Three Days at Gettysburg".