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I'm planning my hitchhiking trip this November 1st and 2nd weeks.

I want to start from Kolkata, enter into Bangladesh, Hitchhike or take public transport towards Agartala, do some sightseeing on the way (if possible) to enter North East India and then, further hitchhike through Northeast which is my final goal.

I have selected Bangladesh as I thought it's kind of shortcut and also I have never been out of India. So, I have no idea about Visa application process too. As an Indian, can I get On-arrival visa into Bangladesh without any hotel bookings or contact numbers in Bangladesh?

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The answer to "can I get On-arrival visa into Bangladesh?" seems to be "No" for an Indian national.

This page "How to get Bangladesh overland visa on arrival" (from a tour agency) states

Please note that Indians are NOT eligible to get Bangladesh visa on arrival in the land borders. They need to apply for a regular visa on the Bangladesh consulates in India.

And according to the Wikipedia page "Visa policy of Bangladesh",

Visa on arrival
According to data provided by IATA, citizens of certain countries may obtain a visa on arrival for the maximum stay of 30 days, except the following

... India ...

Also not all border crossings allow on-demand visas anyway.

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