diff --git a/.env b/.env
index 427a4ab0bf3..eb87dc62bdd 100644
--- a/.env
+++ b/.env
@@ -92,13 +92,13 @@ DEVTOOLSET_VERSION=
 # Used through docker-compose.yml and serves as the default version for the
 # ci/scripts/install_vcpkg.sh script. Prefer to use short SHAs to keep the
 # docker tags more readable.
-VCPKG="501db0f17ef6df184fcdbfbe0f87cde2313b6ab1"    # 2023.04.15 Release
+VCPKG="a42af01b72c28a8e1d7b48107b33e4f286a55ef6"    # 2023.11.20 Release
 
 # This must be updated when we update
-# ci/docker/python-wheel-windows-vs2017.dockerfile.
+# ci/docker/python-wheel-windows-vs2019.dockerfile.
 # This is a workaround for our CI problem that "archery docker build" doesn't
 # use pulled built images in dev/tasks/python-wheels/github.windows.yml.
-PYTHON_WHEEL_WINDOWS_IMAGE_REVISION=2023-08-02
+PYTHON_WHEEL_WINDOWS_IMAGE_REVISION=2024-02-05
 
 # Use conanio/${CONAN} for "docker-compose run --rm conan". See
 # https://github.com/conan-io/conan-docker-tools#readme for available
diff --git a/ci/docker/python-wheel-manylinux.dockerfile b/ci/docker/python-wheel-manylinux.dockerfile
index a07c727ac76..2831440d5a9 100644
--- a/ci/docker/python-wheel-manylinux.dockerfile
+++ b/ci/docker/python-wheel-manylinux.dockerfile
@@ -62,15 +62,16 @@ COPY ci/vcpkg/*.patch \
 COPY ci/scripts/install_vcpkg.sh \
      arrow/ci/scripts/
 ENV VCPKG_ROOT=/opt/vcpkg
-RUN arrow/ci/scripts/install_vcpkg.sh ${VCPKG_ROOT} ${vcpkg}
-ENV PATH="${PATH}:${VCPKG_ROOT}"
-
 ARG build_type=release
 ENV CMAKE_BUILD_TYPE=${build_type} \
     VCPKG_FORCE_SYSTEM_BINARIES=1 \
     VCPKG_OVERLAY_TRIPLETS=/arrow/ci/vcpkg \
     VCPKG_DEFAULT_TRIPLET=${arch_short}-linux-static-${build_type} \
     VCPKG_FEATURE_FLAGS="manifests"
+
+RUN arrow/ci/scripts/install_vcpkg.sh ${VCPKG_ROOT} ${vcpkg}
+ENV PATH="${PATH}:${VCPKG_ROOT}"
+
 COPY ci/vcpkg/vcpkg.json arrow/ci/vcpkg/
 # cannot use the S3 feature here because while aws-sdk-cpp=1.9.160 contains
 # ssl related fixes as well as we can patch the vcpkg portfile to support
diff --git a/ci/docker/python-wheel-windows-test-vs2017.dockerfile b/ci/docker/python-wheel-windows-test-vs2019.dockerfile
similarity index 96%
rename from ci/docker/python-wheel-windows-test-vs2017.dockerfile
rename to ci/docker/python-wheel-windows-test-vs2019.dockerfile
index e842ede1845..67d99fa9c57 100644
--- a/ci/docker/python-wheel-windows-test-vs2017.dockerfile
+++ b/ci/docker/python-wheel-windows-test-vs2019.dockerfile
@@ -19,8 +19,8 @@
 # when you update this file.
 
 # based on mcr.microsoft.com/windows/servercore:ltsc2019
-# contains choco and vs2017 preinstalled
-FROM abrarov/msvc-2017:2.11.0
+# contains choco and vs2019 preinstalled
+FROM abrarov/msvc-2019:2.11.0
 
 # Add unix tools to path
 RUN setx path "%path%;C:\Program Files\Git\usr\bin"
diff --git a/ci/docker/python-wheel-windows-vs2017.dockerfile b/ci/docker/python-wheel-windows-vs2019.dockerfile
similarity index 98%
rename from ci/docker/python-wheel-windows-vs2017.dockerfile
rename to ci/docker/python-wheel-windows-vs2019.dockerfile
index 067105b3a79..b8e8aad952b 100644
--- a/ci/docker/python-wheel-windows-vs2017.dockerfile
+++ b/ci/docker/python-wheel-windows-vs2019.dockerfile
@@ -19,8 +19,8 @@
 # when you update this file.
 
 # based on mcr.microsoft.com/windows/servercore:ltsc2019
-# contains choco and vs2017 preinstalled
-FROM abrarov/msvc-2017:2.11.0
+# contains choco and vs2019 preinstalled
+FROM abrarov/msvc-2019:2.11.0
 
 # Install CMake and Ninja
 ARG cmake=3.21.4
diff --git a/ci/scripts/python_wheel_windows_build.bat b/ci/scripts/python_wheel_windows_build.bat
index ffb43b3481e..73b0192d9bc 100644
--- a/ci/scripts/python_wheel_windows_build.bat
+++ b/ci/scripts/python_wheel_windows_build.bat
@@ -19,7 +19,7 @@
 
 echo "Building windows wheel..."
 
-call "C:\Program Files (x86)\Microsoft Visual Studio\2017\Community\VC\Auxiliary\Build\vcvars64.bat"
+call "C:\Program Files (x86)\Microsoft Visual Studio\2019\Community\VC\Auxiliary\Build\vcvars64.bat"
 
 echo "=== (%PYTHON_VERSION%) Clear output directories and leftovers ==="
 del /s /q C:\arrow-build
@@ -50,7 +50,8 @@ set ARROW_WITH_SNAPPY=ON
 set ARROW_WITH_ZLIB=ON
 set ARROW_WITH_ZSTD=ON
 set CMAKE_UNITY_BUILD=ON
-set CMAKE_GENERATOR=Visual Studio 15 2017 Win64
+set CMAKE_GENERATOR=Visual Studio 16 2019
+set CMAKE_PLATFORM=x64
 set VCPKG_ROOT=C:\vcpkg
 set VCPKG_FEATURE_FLAGS=-manifests
 set VCGPK_TARGET_TRIPLET=amd64-windows-static-md-%CMAKE_BUILD_TYPE%
@@ -96,6 +97,7 @@ cmake ^
     -DVCPKG_MANIFEST_MODE=OFF ^
     -DVCPKG_TARGET_TRIPLET=%VCGPK_TARGET_TRIPLET% ^
     -G "%CMAKE_GENERATOR%" ^
+    -A "%CMAKE_PLATFORM%" ^
     C:\arrow\cpp || exit /B 1
 cmake --build . --config %CMAKE_BUILD_TYPE% --target install || exit /B 1
 popd
@@ -121,6 +123,6 @@ set CMAKE_PREFIX_PATH=C:\arrow-dist
 
 pushd C:\arrow\python
 @REM bundle the msvc runtime
-cp "C:\Program Files (x86)\Microsoft Visual Studio\2017\Community\VC\Redist\MSVC\14.16.27012\x64\Microsoft.VC141.CRT\msvcp140.dll" pyarrow\
+cp "C:\Program Files (x86)\Microsoft Visual Studio\2019\Community\VC\Redist\MSVC\14.28.29325\x64\Microsoft.VC142.CRT\msvcp140.dll" pyarrow\
 python setup.py bdist_wheel || exit /B 1
 popd
diff --git a/ci/vcpkg/ports.patch b/ci/vcpkg/ports.patch
index 68f6cae5add..0d4fb540a20 100644
--- a/ci/vcpkg/ports.patch
+++ b/ci/vcpkg/ports.patch
@@ -1,13 +1,14 @@
 diff --git a/ports/curl/portfile.cmake b/ports/curl/portfile.cmake
-index 5a14562..924b1b7 100644
+index bdc544e9e..53f6bbc3b 100644
 --- a/ports/curl/portfile.cmake
 +++ b/ports/curl/portfile.cmake
-@@ -87,8 +87,11 @@ vcpkg_cmake_configure(
+@@ -74,9 +74,12 @@ vcpkg_cmake_configure(
          -DENABLE_MANUAL=OFF
          -DCURL_CA_FALLBACK=ON
          -DCURL_USE_LIBPSL=OFF
 +        -DCURL_CA_PATH=none
 +        -DCURL_CA_BUNDLE=none
+         -DCMAKE_DISABLE_FIND_PACKAGE_Perl=ON
      OPTIONS_DEBUG
          -DENABLE_DEBUG=ON
 +        ${EXTRA_ARGS_DEBUG}
@@ -15,29 +16,29 @@ index 5a14562..924b1b7 100644
  vcpkg_cmake_install()
  vcpkg_copy_pdbs()
 diff --git a/ports/snappy/portfile.cmake b/ports/snappy/portfile.cmake
-index 8f3f3f9..745b0fb 100644
+index 0c7098082..c603c3653 100644
 --- a/ports/snappy/portfile.cmake
 +++ b/ports/snappy/portfile.cmake
-@@ -9,6 +9,7 @@ vcpkg_from_github(
-     HEAD_REF master
+@@ -10,6 +10,7 @@ vcpkg_from_github(
      PATCHES
          fix_clang-cl_build.patch
+         no-werror.patch
 +        "snappy-disable-bmi.patch"
  )
  
  vcpkg_cmake_configure(
 diff --git a/ports/snappy/snappy-disable-bmi.patch b/ports/snappy/snappy-disable-bmi.patch
 new file mode 100644
-index 0000000..a57ce0c
+index 000000000..e839c93a4
 --- /dev/null
 +++ b/ports/snappy/snappy-disable-bmi.patch
 @@ -0,0 +1,19 @@
 +diff --git a/snappy.cc b/snappy.cc
-+index 79dc0e8..f3153ea 100644
++index d414718..7b49d2a 100644
 +--- a/snappy.cc
 ++++ b/snappy.cc
-+@@ -965,14 +965,10 @@ static inline void Report(const char *algorithm, size_t compressed_size,
-+ static inline uint32_t ExtractLowBytes(uint32_t v, int n) {
++@@ -1014,14 +1014,10 @@ static inline void Report(const char *algorithm, size_t compressed_size,
++ static inline uint32_t ExtractLowBytes(const uint32_t& v, int n) {
 +   assert(n >= 0);
 +   assert(n <= 4);
 +-#if SNAPPY_HAVE_BMI2
@@ -52,13 +53,13 @@ index 0000000..a57ce0c
 + 
 + static inline bool LeftShiftOverflows(uint8_t value, uint32_t shift) {
 diff --git a/ports/llvm/portfile.cmake b/ports/llvm/portfile.cmake
-index 4d7e26a..1f054a2 100644
+index bf9397b66..c3112b673 100644
 --- a/ports/llvm/portfile.cmake
 +++ b/ports/llvm/portfile.cmake
-@@ -274,6 +274,8 @@ vcpkg_cmake_configure(
+@@ -293,6 +293,8 @@ vcpkg_cmake_configure(
+         ${FEATURE_OPTIONS}
+     MAYBE_UNUSED_VARIABLES 
          COMPILER_RT_ENABLE_IOS
-         OPENMP_TOOLS_INSTALL_DIR
-         MLIR_TOOLS_INSTALL_DIR
 +        BOLT_TOOLS_INSTALL_DIR
 +        LIBOMP_INSTALL_ALIASES
  )
diff --git a/ci/vcpkg/vcpkg.json b/ci/vcpkg/vcpkg.json
index 71c23165e61..99771728ecf 100644
--- a/ci/vcpkg/vcpkg.json
+++ b/ci/vcpkg/vcpkg.json
@@ -81,8 +81,11 @@
           "default-features": false,
           "features": [
             "clang",
-            "default-options",
             "default-targets",
+            "enable-bindings",
+            "enable-terminfo",
+            "enable-zlib",
+            "enable-zstd",
             "enable-rtti",
             "lld",
             "tools"
diff --git a/cpp/src/gandiva/CMakeLists.txt b/cpp/src/gandiva/CMakeLists.txt
index 3f038f54a7b..d773fb5ff58 100644
--- a/cpp/src/gandiva/CMakeLists.txt
+++ b/cpp/src/gandiva/CMakeLists.txt
@@ -229,6 +229,15 @@ function(ADD_GANDIVA_TEST REL_TEST_NAME)
 
   set(TEST_NAME gandiva-${REL_TEST_NAME})
   string(REPLACE "_" "-" TEST_NAME ${TEST_NAME})
+
+  if(ARG_USE_STATIC_LINKING OR ARROW_TEST_LINKAGE STREQUAL "static")
+    # LLVM 17 or later requires that an executable exports
+    # "llvm_orc_registerEHFrameSectionWrapper()" and
+    # "llvm_orc_unregisterEHFrameSectionWrapper()". We need to do
+    # nothing when we use libLLVM.so. But we need to export symbols
+    # explicitly when we use libLLVM*.a.
+    set_target_properties(${TEST_NAME} PROPERTIES ENABLE_EXPORTS TRUE)
+  endif()
 endfunction()
 
 add_gandiva_test(internals-test
diff --git a/dev/tasks/python-wheels/github.windows.yml b/dev/tasks/python-wheels/github.windows.yml
index 1641796a719..01f4977a9b0 100644
--- a/dev/tasks/python-wheels/github.windows.yml
+++ b/dev/tasks/python-wheels/github.windows.yml
@@ -29,7 +29,7 @@ jobs:
       # this is a private repository at the moment (mostly because of licensing
       # consideration of windows images with visual studio), but anyone can
       # recreate the image by manually building it via:
-      # `archery build python-wheel-windows-vs2017`
+      # `archery build python-wheel-windows-vs2019`
       # note that we don't run docker build since there wouldn't be a cache hit
       # and rebuilding the dependencies takes a fair amount of time
       REPO: ghcr.io/ursacomputing/arrow
@@ -46,17 +46,17 @@ jobs:
         run: |
           cd arrow
           @rem We want to use only
-          @rem   archery docker run -e SETUPTOOLS_SCM_PRETEND_VERSION={{ arrow.no_rc_version }} python-wheel-windows-vs2017
+          @rem   archery docker run -e SETUPTOOLS_SCM_PRETEND_VERSION={{ arrow.no_rc_version }} python-wheel-windows-vs2019
           @rem but it doesn't use pulled caches.
           @rem It always build an image from scratch.
           @rem We can remove this workaround once we find a way to use
           @rem pulled caches when build an image.
           echo on
-          archery docker pull --no-ignore-pull-failures python-wheel-windows-vs2017
+          archery docker pull --no-ignore-pull-failures python-wheel-windows-vs2019
           if errorlevel 1 (
-            archery docker build --no-pull python-wheel-windows-vs2017 || exit /B 1
+            archery docker build --no-pull python-wheel-windows-vs2019 || exit /B 1
           )
-          archery docker run --no-build -e SETUPTOOLS_SCM_PRETEND_VERSION={{ arrow.no_rc_version }} python-wheel-windows-vs2017
+          archery docker run --no-build -e SETUPTOOLS_SCM_PRETEND_VERSION={{ arrow.no_rc_version }} python-wheel-windows-vs2019
 
       - uses: actions/upload-artifact@v3
         with:
@@ -77,5 +77,5 @@ jobs:
         shell: cmd
         run: |
           cd arrow
-          archery docker push python-wheel-windows-vs2017
+          archery docker push python-wheel-windows-vs2019
       {% endif %}
diff --git a/docker-compose.yml b/docker-compose.yml
index 0252c4ec8a8..09e7fe27bbc 100644
--- a/docker-compose.yml
+++ b/docker-compose.yml
@@ -172,7 +172,7 @@ x-hierarchy:
   - python-wheel-manylinux-2-28
   - python-wheel-manylinux-test-imports
   - python-wheel-manylinux-test-unittests
-  - python-wheel-windows-vs2017
+  - python-wheel-windows-vs2019
   - python-wheel-windows-test
 
 volumes:
@@ -1098,19 +1098,19 @@ services:
       CHECK_UNITTESTS: "ON"
     command: /arrow/ci/scripts/python_wheel_unix_test.sh /arrow
 
-  python-wheel-windows-vs2017:
-    image: ${REPO}:python-${PYTHON}-wheel-windows-vs2017-vcpkg-${VCPKG}-${PYTHON_WHEEL_WINDOWS_IMAGE_REVISION}
+  python-wheel-windows-vs2019:
+    image: ${REPO}:python-${PYTHON}-wheel-windows-vs2019-vcpkg-${VCPKG}-${PYTHON_WHEEL_WINDOWS_IMAGE_REVISION}
     build:
       args:
         vcpkg: ${VCPKG}
         python: ${PYTHON}
       context: .
-      dockerfile: ci/docker/python-wheel-windows-vs2017.dockerfile
+      dockerfile: ci/docker/python-wheel-windows-vs2019.dockerfile
       # This should make the pushed images reusable, but the image gets rebuilt.
       # Uncomment if no local cache is available.
       # cache_from:
-      #   - abrarov/msvc-2017:2.11.0
-      #   - ${REPO}:python-${PYTHON}-wheel-windows-vs2017-vcpkg-${VCPKG}-${PYTHON_WHEEL_WINDOWS_IMAGE_REVISION}
+      #   - abrarov/msvc-2019:2.11.0
+      #   - ${REPO}:python-${PYTHON}-wheel-windows-vs2019-vcpkg-${VCPKG}-${PYTHON_WHEEL_WINDOWS_IMAGE_REVISION}
     volumes:
       - "${DOCKER_VOLUME_PREFIX}python-wheel-windows-clcache:C:/clcache"
       - type: bind
@@ -1119,12 +1119,12 @@ services:
     command: arrow\\ci\\scripts\\python_wheel_windows_build.bat
 
   python-wheel-windows-test:
-    image: ${REPO}:python-${PYTHON}-wheel-windows-test-vs2017-${PYTHON_WHEEL_WINDOWS_IMAGE_REVISION}
+    image: ${REPO}:python-${PYTHON}-wheel-windows-test-vs2019-${PYTHON_WHEEL_WINDOWS_IMAGE_REVISION}
     build:
       args:
         python: ${PYTHON}
       context: .
-      dockerfile: ci/docker/python-wheel-windows-test-vs2017.dockerfile
+      dockerfile: ci/docker/python-wheel-windows-test-vs2019.dockerfile
     volumes:
       - "${DOCKER_VOLUME_PREFIX}python-wheel-windows-clcache:C:/clcache"
       - type: bind