diff --git a/.github/workflows/cpp.yml b/.github/workflows/cpp.yml
index 1d681c96a75..f546260bc50 100644
--- a/.github/workflows/cpp.yml
+++ b/.github/workflows/cpp.yml
@@ -197,12 +197,21 @@ jobs:
     strategy:
       fail-fast: false
       matrix:
-        os:
-          - windows-2019
         include:
           - os: windows-2019
-            name: Windows 2019
+            name: Windows 2019 x64
             generator: Visual Studio 16 2019
+            platform: x64
+            openssl-n-bits: 64
+            program-files-dir: Program Files
+            chocolate-force:
+          - os: windows-2019
+            name: Windows 2019 Win32
+            generator: Visual Studio 16 2019
+            platform: Win32
+            openssl-n-bits: 32
+            program-files-dir: Program Files (x86)
+            chocolate-force: --forcex86
     env:
       ARROW_BOOST_USE_SHARED: OFF
       ARROW_BUILD_BENCHMARKS: ON
@@ -227,7 +236,7 @@ jobs:
       ARROW_WITH_ZLIB: ON
       ARROW_WITH_ZSTD: ON
       BOOST_SOURCE: BUNDLED
-      CMAKE_ARGS: '-A x64 -DOPENSSL_ROOT_DIR=C:\Program Files\OpenSSL-Win64'
+      CMAKE_ARGS: '-A ${{ matrix.platform }} -DOPENSSL_ROOT_DIR=C:/${{ matrix.program-files-dir }}/OpenSSL-Win${{ matrix.openssl-n-bits }}'
       CMAKE_GENERATOR: ${{ matrix.generator }}
       CMAKE_INSTALL_LIBDIR: bin
       CMAKE_INSTALL_PREFIX: /usr
@@ -245,7 +254,7 @@ jobs:
       - name: Installed Packages
         run: choco list -l
       - name: Install Dependencies
-        run: choco install -y --no-progress openssl
+        run: choco install -y --no-progress ${{ matrix.chocolate-force }} openssl
       - name: Checkout Arrow
         uses: actions/checkout@v3
         with:
diff --git a/cpp/src/arrow/util/bit_util.h b/cpp/src/arrow/util/bit_util.h
index 8583e10b226..b5414b34511 100644
--- a/cpp/src/arrow/util/bit_util.h
+++ b/cpp/src/arrow/util/bit_util.h
@@ -67,7 +67,14 @@ static constexpr uint8_t kBytePopcount[] = {
     5, 4, 5, 5, 6, 3, 4, 4, 5, 4, 5, 5, 6, 4, 5, 5, 6, 5, 6, 6, 7, 3, 4, 4, 5, 4, 5, 5, 6,
     4, 5, 5, 6, 5, 6, 6, 7, 4, 5, 5, 6, 5, 6, 6, 7, 5, 6, 6, 7, 6, 7, 7, 8};
 
-static inline uint64_t PopCount(uint64_t bitmap) { return ARROW_POPCOUNT64(bitmap); }
+static inline uint64_t PopCount(uint64_t bitmap) {
+#if defined(_MSC_VER) && !defined(_M_AMD64) && !defined(_M_X64)
+  return ARROW_POPCOUNT32((bitmap >> 32) & UINT32_MAX) +
+         ARROW_POPCOUNT32(bitmap & UINT32_MAX);
+#else
+  return ARROW_POPCOUNT64(bitmap);
+#endif
+}
 static inline uint32_t PopCount(uint32_t bitmap) { return ARROW_POPCOUNT32(bitmap); }
 
 //
@@ -199,7 +206,7 @@ static inline int CountLeadingZeros(uint64_t value) {
 #if defined(__clang__) || defined(__GNUC__)
   if (value == 0) return 64;
   return static_cast<int>(__builtin_clzll(value));
-#elif defined(_MSC_VER)
+#elif defined(_MSC_VER) && (defined(_M_AMD64) || defined(_M_X64))
   unsigned long index;                     // NOLINT
   if (_BitScanReverse64(&index, value)) {  // NOLINT
     return 63 - static_cast<int>(index);
@@ -245,7 +252,7 @@ static inline int CountTrailingZeros(uint64_t value) {
 #if defined(__clang__) || defined(__GNUC__)
   if (value == 0) return 64;
   return static_cast<int>(__builtin_ctzll(value));
-#elif defined(_MSC_VER)
+#elif defined(_MSC_VER) && (defined(_M_AMD64) || defined(_M_X64))
   unsigned long index;  // NOLINT
   if (_BitScanForward64(&index, value)) {
     return static_cast<int>(index);
@@ -255,7 +262,7 @@ static inline int CountTrailingZeros(uint64_t value) {
 #else
   int bitpos = 0;
   if (value) {
-    while (value & 1 == 0) {
+    while ((value & 1) == 0) {
       value >>= 1;
       ++bitpos;
     }
diff --git a/cpp/src/arrow/util/io_util.cc b/cpp/src/arrow/util/io_util.cc
index 11ae80d03e2..26afc9a23fa 100644
--- a/cpp/src/arrow/util/io_util.cc
+++ b/cpp/src/arrow/util/io_util.cc
@@ -1439,7 +1439,8 @@ Status MemoryAdviseWillNeed(const std::vector<MemoryRegion>& regions) {
     PrefetchEntry(const MemoryRegion& region)  // NOLINT runtime/explicit
         : VirtualAddress(region.addr), NumberOfBytes(region.size) {}
   };
-  using PrefetchVirtualMemoryFunc = BOOL (*)(HANDLE, ULONG_PTR, PrefetchEntry*, ULONG);
+  using PrefetchVirtualMemoryFunc =
+      BOOL(__stdcall*)(HANDLE, ULONG_PTR, PrefetchEntry*, ULONG);
   static const auto prefetch_virtual_memory = reinterpret_cast<PrefetchVirtualMemoryFunc>(
       GetProcAddress(GetModuleHandleW(L"kernel32.dll"), "PrefetchVirtualMemory"));
   if (prefetch_virtual_memory != nullptr) {