If you are looking for a vectorized way of doing this (which you probably should be), you can use something like the code below.
The fundamental idea behind this is to find the difference between the current time in your timezone and the UTC time. In the winter months, the difference will be one extra hour behind UTC. Whatever the difference is, add what is needed to get to the 1 or 0 for the flag.
In Denver, summer months are UTC-6 and winter months are UTC-7. So, if you take the difference between the tz-aware time in Denver and UTC time, then add 7, you'll get a value of 1 for summer months and a value of 0 for winter months.
import pandas as pd
start = pd.to_datetime('2020-10-30')
end = pd.to_datetime('2020-11-02')
dates = pd.date_range(start=start, end=end, freq='h', tz='America/Denver')
df1 = pd.DataFrame({'dst_flag': 1, 'date1': dates.tz_localize(None)}, index=dates)
# add extra day on each end so that there are no nan's after the join
dates = pd.to_datetime(pd.date_range(start=start - pd.to_timedelta(1, 'd'), end=end + pd.to_timedelta(1, 'd'), freq='h'), utc=True)
df2 = pd.DataFrame({'date2': dates.tz_localize(None)}, index=dates)
out = df1.join(df2)
out['dst_flag'] = (out['date1'] - out['date2']) / pd.to_timedelta(1, unit='h') + 7
out.drop(columns=['date1', 'date2'], inplace=True)