Red Dead Redemption's multi-player Free Roam offers a vast open landscape with five different challenge categories: Sharpshooter, Hunter, Survivalist, Lawbringer and Outlaw. Keeping track of your Free Roam Challenges is as simple as pausing the game, choosing 'Journal' and then 'Free Roam'.Part one of a series of tips on ways to conquer the Free Roam challenges, starting off with Sharpshooter and Hunter:
Sharpshooter I
Shoot and kill five flying birds to earn 250 XP and the title Bird Watcher.
Tip: Enter an open grassy area such as Hennigan's Stead. Fire off a shot to see and hear if any birds are nearby.
Shoot and kill five rabbits to earn 250 XP and the title Exterminator.
Tip: Search around MacFarlane's Ranch for these critters.
Get ten head shots on enemy AI to get 250 XP and the title Head Hollower.
Tip: Go to a Gang Hideout such as Twin Rocks and use the Rolling Block Rifle or the Carcano Rifle. Enemies will take defensive positions and allow you to easily pick them off.
Shoot ten guns out of enemies' hands to earn 250 XP and the title Sharpshooter.
Tip: Target enemy gun hands with Dead Eye.
Sharpshooter II
Shoot two hats off of two different people's heads within five seconds of each other to earn 250 XP and the title Hat Trickster.
Tip: Head to a Gang Hideout where the enemies have large hats such as Twin Rocks. Use Dead Eye for accuracy.
Shoot someone's hat off and shoot the gun out of their hand within three seconds of each other to earn 250 XP and the title Hauty Gunhand.
Tip: Use Dead Eye to mark the top of an enemy's hat and also his gun hand.
Kill a grizzly bear with a single head shot to earn 250 XP and the title Bear Starer.
Tip: Find grizzly bears in Tall Trees north of Manzanita Post. Use a weapon such as the Semi-Auto Shotgun at close range.
Shoot a hat off someone while riding a mount to earn 250 XP and the title Hat Flyer.
Tip: A Gang Hideout such as Tesoro Azul has enemies with larger hats that are easier to target and shoot.
Kill any three different types of wild animals within ten seconds of each other to earn 250 XP and the title Master Sharpshooter.
Tip: Tall Trees is where you'll find an abundance of wildlife: wild boars, elk, bears, bighorns, deer and foxes.
Hunter I
Kill five deer to earn 250 XP and the title Stew Brewer.
Tip: Deer can be found in the northern section of Tall Trees, Gaptooth Ridge, south of Roca de Madera in Diez Coronas as well as many other places.
Kill five coyotes to earn 250 XP and the title Conservationist.
Tip: Ride around the outskirts of Armadillo and listen for the sounds of the coyotes.
Kill five wolves (one must be with a knife) to earn 250 XP and the title Wolf Cryer.
Tip: Wolves can be found in several places. Some of them are Torquemada, Rio del Lobo, north of Ridgewood Farm and north of Chuparosa.
Kill five cougars (one must be with a knife) to earn 250 XP and the title The Mauled.
Tip: Look in Gaptooth Ridge or Rio Bravo.
Kill five elk and five bighorn to earn 250 XP and the title Hunter.
Tip: The northernmost area of Tall Trees is your best bet for finding elk and bighorn.
Hunter II
Kill five bears (one must be with a knife) to earn 250 XP and the title Spartan Survival.
Tip: The northern and snowy section of Tall Trees is where you'll find the bears.
Find and kill a unique named wolf to earn 250 XP and the title Lycanthropist.
Tip: Lobo the wolf is located in Barranca just southeast of Chuparosa.
Find and kill a unique named giant boar to earn 250 XP and the title Lord of the Flies.
Tip: Gordo the boar is located in Greenhollow on the New Austin side of the border opposite El Presidio.
Find and kill a unique named giant jaguar to earn 250 XP and the title Cat Ballyhoo.
Tip: Khan the jaguar is located in Tanner’s Reach, west of Manzanita Post and south of Aurora Basin.
Find and kill a unique named giant bear to earn 250 XP and the title Master Hunter.
Tip: Brumas the bear is located in the Southern section of Tall Trees at Bearclaw Camp.
From the official blog here