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Matheran was a name I had often heard of, but never really inquired about; i.e. till recently when a long weekend came and hence the plans to travel.
Before I reached the place, all I knew was how to reach and nothing really much about the place itself. I didn't even know the place I was staying in, and could reach the desired destination only after reaching another nice resort and demanding my missing room and missing wife!
The best season to travel to Matheran is the monsoon, which is fairly long here. However, its also the season when the charming toy train stops plying between Neral and Matheran. Reaching Neral is easy, local trains from Mumbai every hour, see the schedule here, and a number of trains from Pune as well. There are taxis from Neral which take you to Matheran, about 8 km (half an hour) away on a hill close by. Once you pay the entrance fee at the gate you enter into a eco-zone i.e. no vehicles (except the local ambulance) allowed.
You can either walk or take a horse. The distance is decent (about 4 km) and takes about half an hour on the horse, walking of course is slower, healthier and possibly more fun.
My horse-man told me that there are three nice places to stay in Matheran - The Byke, Usha Ascot and The Woodlands. I stayed at The Byke, which is a heritage building converted into a hotel, and the experience was nice. It has numerous cottages, a pool, bar etc. Many families stay there, and that could be an irritant. However, late nights are peaceful and walking around the place sheer delight.
I suggest spending a couple of days at least in the town, it takes that much time to soak in all the beauty of the place. Nothing worth visiting is close by, and good sneakers are a must. Even on a tourist-heavy weekend, there are long stretches where you can walk in solitude with only an occasional fellow traveler. You can walk anytime into the jungle, climb trees, walk down into a pit or simply look down into the green valley. And that rings me to Green. The lasting memory of Matheran is Green, it green everywhere (apart from the earthy brown). You are inspired to do weird stuff when you see such greenery around, like taking snaps straight out of Chandni poster :) But its totally fun, and you come back with everlasting memories, even though you might laugh at it together at a later date.
I leave it to the traveler to discover the place, there are numerous websites, blogs etc which give information on what to see etc. I followed none and just allowed the place to lead. Its rewarding when you see places which you have not at all seen earlier anywhere (i.e. google images). But I guess it works both ways, its a matter of personal preference.
And if you love getting into the water, do carry a pair of swimming trunks. There are numerous seasonal springs which allow splashing water, plus the pool in your resort could also be used.