Duration: About a 1 hour walk up to however long if you shop.
Difficulty: Easy. Flat.
Appreciation: 8/10 if you want to soak in the culture.
Transportation: Start from the Sheung Wan MTR station, exit 'B'.Why it's worth it: Go when the stores are open. You'll see a bit of what's typical of Hong Kong. A few key historic sites. Do so antique shopping.
1. Western Market: Edwardian Building built in the early 20th century. You can get in a browse the various shops.
Once you're done, make your way to the Wing Lok street and check out the Bird's Nest and Ginseng shops.
Keep going until you reach DesVoeux road. At DesVoeux/Queens/Ko Shing, you'll see an escalator going up a building. That's a hot food market. If you haven't had lunch, you may want to pause and mingle with the local for cheap fares in an unfamiliar setting.
Once your belly is full, come back down and keep going on DesVoeux where you will find many dried seafood shops. Step in and have a look if your nose can tolerate. Dried seafood is used in many of the everyday Cantonese dishes.
Upon arriving at Ko Shing Street, turn left onto it. You will discover tons of herbal medicine shops. If anything ails you, there might even be a local Chinese doctor to recommend some highly "fragrant" concoction to make you better. Keep walking to WoFung road, then via Wo Fung to Hollywwod Road. "Hollywood Road was the second road to be built when the colony of Hong Kong was founded, after Queen's Road. It was the first to be completed. Some people think that the road was named after the box-office success of the illustrious movieland flick, The World of Suzie Wong. In fact the road was put up early in 1844, at least forty years before the more famous Hollywood in California was settled. It was named after Hollywood, the family home of Hong Kong's second British governor, Sir John Francis Davis, near Bristol, England. " (Wikipedia)
2. Possesion Point.
Walk a little bit on Holliwood until you reach Possession Point (now Hollywood Road Park). "The area is where Commodore James Bremer, commander-in-chief of the British forces in China, took formal possession of Hong Kong on 26 January 1841." (Wikipedia)
Now, stop and think for a minute that Possession Point used to be on the coast! That's land reclamation for you!
On Holywood Road, you will find a myriad on antiques shops. Take your time to explore. Although unaffordable for most people, those treasures are worth a look.
3. ManMo Temple
Strolling along Hollywood, you will reach the ManMo temple; "A Man Mo Temple or Man Mo Miu (traditional Chinese: 文武廟) is a temple for the worship of the civil or literature god Man Tai (文帝) / Man Cheong （文昌） and the martial god Mo Tai (武帝) / Kwan Tai (關帝). The two gods were popularly patronized by scholars and students seeking progress in their study or ranking in the civil examinations in the Ming and Qing dynasties." (Wikipedia)
From this point on, I suggest you keep going on Hollywood and visit more of those antiques shops, until you reach the escalator. If time permits, you can visit the old Police Station and its prison, or go up the escalator to SoHo for drinks before dinner, or down towards the MTR and the IFC mall and ferry pier.