diff --git a/doc/source/whatsnew/v3.1.0.rst b/doc/source/whatsnew/v3.1.0.rst
index 86d7507553714..68899cd12543b 100644
--- a/doc/source/whatsnew/v3.1.0.rst
+++ b/doc/source/whatsnew/v3.1.0.rst
@@ -482,6 +482,7 @@ Groupby/resample/rolling
 Reshaping
 ^^^^^^^^^
 - Bug in :func:`concat` raising ``InvalidIndexError`` when ``keys`` or the concatenated objects' index was an overlapping :class:`IntervalIndex` (:issue:`64825`)
+- Bug in :func:`concat` where the frequency of the combined :class:`DatetimeIndex` depended on the order of the concatenated objects when they shared a non-inferable frequency such as :class:`~pandas.tseries.offsets.CustomBusinessDay` (:issue:`64253`)
 - Bug in :func:`merge` where merging on a :class:`MultiIndex` containing ``NaN`` values mapped ``NaN`` keys to the last level value instead of ``NaN`` (:issue:`64492`)
 - Bug in :meth:`DataFrame.melt` where ``var_name`` colliding with an ``id_vars`` column or ``value_name`` silently overwrote the affected column data instead of raising (:issue:`65654`)
 - Bug in :meth:`DataFrame.pivot_table` with ``margins=True`` raising ``TypeError`` when ``values`` has an :class:`ExtensionDtype` that cannot hold ``NA`` (e.g. :class:`IntervalDtype` with an integer subtype) and no ``columns`` were specified (:issue:`55484`)
diff --git a/pandas/core/indexes/api.py b/pandas/core/indexes/api.py
index 89666f763d42b..55ea3c639f866 100644
--- a/pandas/core/indexes/api.py
+++ b/pandas/core/indexes/api.py
@@ -23,7 +23,10 @@
     maybe_sequence_to_range,
 )
 from pandas.core.indexes.category import CategoricalIndex
-from pandas.core.indexes.datetimes import DatetimeIndex
+from pandas.core.indexes.datetimes import (
+    DatetimeIndex,
+    date_range,
+)
 from pandas.core.indexes.interval import IntervalIndex
 from pandas.core.indexes.multi import MultiIndex
 from pandas.core.indexes.period import PeriodIndex
@@ -145,6 +148,10 @@ def _get_combined_index(
 
     if sort and sort is not lib.no_default:
         index = safe_sort_index(index)
+    if not intersect:
+        # GH#64253: keep the combined-index freq order-independent even when an
+        # explicit sort rebuilds the index (which would otherwise drop freq).
+        index = _restore_shared_datetime_freq(index, indexes)
     return index
 
 
@@ -182,6 +189,35 @@ def safe_sort_index(index: Index) -> Index:
     return index
 
 
+def _restore_shared_datetime_freq(result: Index, indexes: list[Index]) -> Index:
+    """
+    Reattach a shared, non-inferable frequency to a combined ``DatetimeIndex``.
+
+    A pairwise union of ``DatetimeIndex`` objects can drop a shared frequency in
+    an intermediate step (e.g. a ``CustomBusinessDay`` freq, which cannot be
+    recovered by ``inferred_freq``), leaving ``result.freq`` dependent on the
+    order of the inputs (GH#64253). If every input shares a single frequency and
+    ``result`` is exactly regular with respect to it, reattach that frequency so
+    the combined index does not depend on the input order. ``result`` is
+    returned unchanged (values and dtype untouched) in every other case.
+    """
+    if (
+        not isinstance(result, DatetimeIndex)
+        or result.freq is not None
+        or len(result) < 3
+    ):
+        return result
+    freqs = {getattr(idx, "freq", None) for idx in indexes}
+    if len(freqs) != 1:
+        return result
+    freq = next(iter(freqs))
+    if freq is None:
+        return result
+    if result.equals(date_range(result[0], result[-1], freq=freq, unit=result.unit)):
+        return result._with_freq(freq)
+    return result
+
+
 def union_indexes(indexes, sort: bool | lib.NoDefault = True) -> Index:
     """
     Return the union of indexes.
@@ -246,6 +282,11 @@ def union_indexes(indexes, sort: bool | lib.NoDefault = True) -> Index:
 
         for other in indexes[1:]:
             result = result.union(other, sort=None if sort else False)
+
+        if num_dtis == len(indexes):
+            # GH#64253: a pairwise union can drop a shared, non-inferable freq
+            # in an intermediate step, making result.freq order-dependent.
+            result = _restore_shared_datetime_freq(result, indexes)
         return result
 
     elif kind == "array":
diff --git a/pandas/tests/reshape/concat/test_datetimes.py b/pandas/tests/reshape/concat/test_datetimes.py
index dee0dda326129..a4e298900effb 100644
--- a/pandas/tests/reshape/concat/test_datetimes.py
+++ b/pandas/tests/reshape/concat/test_datetimes.py
@@ -136,6 +136,25 @@ def test_concat_datetimeindex_freq_mixed_unit(self):
         # Not checked by assert_index_equal
         assert result.freq == "s"
 
+    def test_concat_datetimeindex_freq_order_independent(self):
+        # GH#64253 - the freq of the combined index must not depend on the
+        # order of the inputs when they share a (non-inferable) freq and the
+        # union is exactly regular with respect to it.
+        freq = pd.offsets.CustomBusinessDay(holidays=["2020-01-10"])
+        idx1 = date_range("2020-01-01", periods=5, freq=freq)
+        idx2 = date_range(start=idx1[3], periods=5, freq=freq)
+        idx3 = date_range(start=idx2[3], periods=5, freq=freq)
+        s1 = Series(1, index=idx1, name="S1")
+        s2 = Series(1, index=idx2, name="S2")
+        s3 = Series(1, index=idx3, name="S3")
+
+        result_123 = concat([s1, s2, s3], axis=1, sort=True)
+        result_132 = concat([s1, s3, s2], axis=1, sort=True)
+
+        assert result_123.index.freq == freq
+        assert result_132.index.freq == freq
+        tm.assert_index_equal(result_123.index, result_132.index)
+
     def test_concat_datetimeindex_tz_convert_freq(self):
         # GH#41585 - concat after tz_convert should not raise when
         # the converted timestamps no longer conform to the original freq