Timing
Most of these hills can be arranged at a few weeks' notice. The exceptions are the dates where rooms, seats or permits decide when you should write, and the planning page lists them one by one.
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Paro Tshechu, March or April
The Paro valley books up for the masked dances, and rooms are requested as soon as the lunar dates are published. Bhutan in October, November or spring needs six months or more, because the lodge rooms guests ask for most go first.
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Tihar, in the hills
Holiday traffic from the plains fills the good houses in Diwali week. Tihar runs from 7 to 11 November 2026; for this year, the advice is to write now, and the designer tells you plainly which houses still have rooms.
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Christmas
Heritage rooms are few. The MAYFAIR in Kalimpong has seven and a suite in its original building, each with a fireplace, so a Christmas in the hills is best written for by September.
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Tea estates
Glenburn has eight suites in all and takes full payment 30 days before arrival, so in peak season write three months or more ahead. It also asks three months' notice to embroider your initials on its pillowcases.
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The steam joy ride
Indian Railways opens seats 60 days before travel, and the team books on the day they open. If a set day on the steam joy ride matters to you, confirm before that mark.
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Paperwork
For foreign or OCI guests, Sikkim's Restricted Area Permit is issued only online through e-FRRO, about 30 days before you reach the state. Bhutan on an Indian passport needs ID scans about six weeks out; the Goecha La trek, 30 days.
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Short notice
Darjeeling and Kalimpong need no permits, so a late trip there depends only on rooms and cars. A journey confirmed inside 45 days of travel is paid in full at confirmation. A month and a headcount are enough to begin.
Photo: Mosharraf Hossain / Unsplash