diff --git a/dev/tasks/r/github.linux.version.compatibility.yml b/dev/tasks/r/github.linux.version.compatibility.yml
new file mode 100644
index 00000000000..2f64227eb8d
--- /dev/null
+++ b/dev/tasks/r/github.linux.version.compatibility.yml
@@ -0,0 +1,109 @@
+# Licensed to the Apache Software Foundation (ASF) under one
+# or more contributor license agreements.  See the NOTICE file
+# distributed with this work for additional information
+# regarding copyright ownership.  The ASF licenses this file
+# to you under the Apache License, Version 2.0 (the
+# "License"); you may not use this file except in compliance
+# with the License.  You may obtain a copy of the License at
+#
+#   http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing,
+# software distributed under the License is distributed on an
+# "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY
+# KIND, either express or implied.  See the License for the
+# specific language governing permissions and limitations
+# under the License.
+
+# NOTE: must set "Crossbow" as name to have the badge links working in the
+# github comment reports!
+name: Crossbow
+
+on:
+  push
+
+jobs:
+  write-files:
+    name: "Write files"
+    runs-on: ubuntu-20.04
+    strategy:
+      fail-fast: false
+    env:
+      ARROW_R_DEV: "TRUE"
+      RSPM: "https://packagemanager.rstudio.com/cran/__linux__/focal/latest"
+    steps:
+      - name: Checkout Arrow
+        run: |
+          git clone --no-checkout {{ arrow.remote }} arrow
+          git -C arrow fetch -t {{ arrow.remote }} {{ arrow.branch }}
+          git -C arrow checkout FETCH_HEAD
+          git -C arrow submodule update --init --recursive
+      - name: Free Up Disk Space
+        shell: bash
+        run: arrow/ci/scripts/util_cleanup.sh
+      - name: Fetch Submodules and Tags
+        shell: bash
+        run: cd arrow && ci/scripts/util_checkout.sh
+      - uses: r-lib/actions/setup-r@v1
+      - name: Install dependencies
+        run: |
+          install.packages(c("remotes", "glue", "sys"))
+          remotes::install_deps("arrow/r", dependencies = TRUE)
+        shell: Rscript {0}
+      - name: Install Arrow
+        run: |
+          cd arrow/r
+          R CMD INSTALL .
+        shell: bash
+      - name: Write files
+        run: |
+          cd arrow/r
+          R -f extra-tests/write-files.R
+        shell: bash
+
+      - name: Upload the parquet artifacts
+        uses: actions/upload-artifact@v2
+        with:
+          name: files
+          path: arrow/r/extra-tests/files
+
+  read-files:
+    name: "Read files with Arrow {{ '${{ matrix.old_arrow_version }}' }}"
+    needs: [write-files]
+    runs-on: ubuntu-20.04
+    strategy:
+      fail-fast: false
+      matrix:
+        old_arrow_version:
+          - "2.0.0"
+          - "1.0.1"
+    env:
+      RSPM: "https://packagemanager.rstudio.com/cran/__linux__/focal/latest"
+      OLD_ARROW_VERSION: {{ '${{ matrix.old_arrow_version }}' }}
+    steps:
+      - name: Checkout Arrow
+        run: |
+          git clone --no-checkout {{ arrow.remote }} arrow
+          git -C arrow fetch -t {{ arrow.remote }} {{ arrow.branch }}
+          git -C arrow checkout FETCH_HEAD
+          git -C arrow submodule update --init --recursive
+      - uses: r-lib/actions/setup-r@v1
+      - name: Install old Arrow
+        run: |
+          install.packages(c("remotes", "testthat"))
+          remotes::install_version("arrow",  "{{ '${{ matrix.old_arrow_version }}' }}")
+        shell: Rscript {0}
+      - name: Setup our testing directory, copy only the tests to it.
+        run: |
+          mkdir -p extra-tests/files
+          cp arrow/r/extra-tests/helper*.R extra-tests/
+          cp arrow/r/extra-tests/test-*.R extra-tests/
+      - name: Download artifacts
+        uses: actions/download-artifact@v2
+        with:
+          name: files
+          path: extra-tests/files
+      - name: Test reading
+        run: |
+          testthat::test_dir("extra-tests")
+        shell: Rscript {0}
diff --git a/dev/tasks/tasks.yml b/dev/tasks/tasks.yml
index 569e59f80dd..79bc120cf72 100644
--- a/dev/tasks/tasks.yml
+++ b/dev/tasks/tasks.yml
@@ -1752,6 +1752,10 @@ tasks:
     template: r/github.linux.cran.yml
     params:
       MATRIX: "${{ matrix.r_image }}"
+      
+  test-r-version-compatibility:
+    ci: github
+    template: r/github.linux.version.compatibility.yml
 
   test-r-rhub-ubuntu-gcc-release:
     ci: azure
diff --git a/r/.Rbuildignore b/r/.Rbuildignore
index 91a8d741a8e..cf4b7ce31ba 100644
--- a/r/.Rbuildignore
+++ b/r/.Rbuildignore
@@ -23,3 +23,4 @@ clang_format.sh
 ^autobrew$
 ^apache-arrow.rb$
 ^.*\.Rhistory$
+^extra-tests
diff --git a/r/.gitignore b/r/.gitignore
index e5ab1197071..76e8a8dd0bd 100644
--- a/r/.gitignore
+++ b/r/.gitignore
@@ -17,3 +17,4 @@ revdep/
 vignettes/nyc-taxi/
 arrow_*.tar.gz
 arrow_*.tgz
+extra-tests/files
diff --git a/r/extra-tests/helpers.R b/r/extra-tests/helpers.R
new file mode 100644
index 00000000000..61b7da4ec25
--- /dev/null
+++ b/r/extra-tests/helpers.R
@@ -0,0 +1,32 @@
+# Licensed to the Apache Software Foundation (ASF) under one
+# or more contributor license agreements.  See the NOTICE file
+# distributed with this work for additional information
+# regarding copyright ownership.  The ASF licenses this file
+# to you under the Apache License, Version 2.0 (the
+# "License"); you may not use this file except in compliance
+# with the License.  You may obtain a copy of the License at
+#
+#   http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing,
+# software distributed under the License is distributed on an
+# "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY
+# KIND, either express or implied.  See the License for the
+# specific language governing permissions and limitations
+# under the License.
+
+if_version <- function(version, op = `==`) {
+  op(packageVersion("arrow"), version)
+}
+
+skip_if_version_less_than <- function(version, msg) {
+  if(if_version(version, `<`)) {
+    skip(msg)
+  }
+}
+
+skip_if_version_equals <- function(version, msg) {
+  if(if_version(version, `==`)) {
+    skip(msg)
+  }
+}
diff --git a/r/extra-tests/test-read-files.R b/r/extra-tests/test-read-files.R
new file mode 100644
index 00000000000..90efce3d791
--- /dev/null
+++ b/r/extra-tests/test-read-files.R
@@ -0,0 +1,165 @@
+# Licensed to the Apache Software Foundation (ASF) under one
+# or more contributor license agreements.  See the NOTICE file
+# distributed with this work for additional information
+# regarding copyright ownership.  The ASF licenses this file
+# to you under the Apache License, Version 2.0 (the
+# "License"); you may not use this file except in compliance
+# with the License.  You may obtain a copy of the License at
+#
+#   http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing,
+# software distributed under the License is distributed on an
+# "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY
+# KIND, either express or implied.  See the License for the
+# specific language governing permissions and limitations
+# under the License.
+
+library(arrow)
+library(testthat)
+
+pq_file <- "files/ex_data.parquet"
+
+test_that("Can read the file (parquet)", {
+  # We can read with no error, we assert metadata below
+  expect_error(
+    df <- read_parquet(pq_file),
+    NA
+  )
+})
+
+### Parquet
+test_that("Can see the metadata (parquet)", {
+  skip_if_version_less_than("2.0.0", "Version 1.0.1 can't read new version metadata.")
+
+  df <- read_parquet(pq_file)
+  expect_s3_class(df, "tbl")
+
+  expect_equal(
+    attributes(df),
+    list(
+      names = letters[1:4],
+      row.names = 1L,
+      top_level = list(
+        field_one = 12,
+        field_two = "more stuff"
+      ),
+      class = c("tbl_df", "tbl", "data.frame")
+    )
+  )
+
+  # column-level attributes
+  expect_equal(attributes(df$a), list(class = "special_string"))
+  expect_equal(
+    attributes(df$c),
+    list(
+      row.names = 1L,
+      names = c("c1", "c2", "c3"),
+      class = c("tbl_df", "tbl", "data.frame")
+    )
+  )
+})
+
+### Feather
+for (comp in c("lz4", "uncompressed", "zstd")) {
+  feather_file <- paste0("files/ex_data_", comp, ".feather")
+
+  test_that(paste0("Can read the file (feather ", comp, ")"), {
+    # We can read with no error, we assert metadata below
+    expect_error(
+      df <- read_feather(feather_file),
+      NA
+    )
+  })
+
+  test_that(paste0("Can see the metadata (feather ", comp, ")"), {
+    skip_if_version_less_than("2.0.0", "Version 1.0.1 can't read new version metadata.")
+
+    df <- read_feather(feather_file)
+    expect_s3_class(df, "tbl")
+
+    expect_equal(
+      attributes(df),
+      list(
+        names = letters[1:4],
+        row.names = 1L,
+        top_level = list(
+          field_one = 12,
+          field_two = "more stuff"
+        ),
+        class = c("tbl_df", "tbl", "data.frame")
+      )
+    )
+
+    # column-level attributes
+    expect_equal(attributes(df$a), list(class = "special_string"))
+    expect_equal(
+      attributes(df$c),
+      list(
+        row.names = 1L,
+        names = c("c1", "c2", "c3"),
+        class = c("tbl_df", "tbl", "data.frame")
+      )
+    )
+  })
+}
+
+test_that("Can read feather version 1", {
+  feather_v1_file <- "files/ex_data_v1.feather"
+
+  df <- read_feather(feather_v1_file)
+  expect_s3_class(df, "tbl")
+
+  expect_equal(
+    attributes(df),
+    list(
+      names = c("a", "b", "d"),
+      class = c("tbl_df", "tbl", "data.frame"),
+      row.names = 1L
+    )
+  )
+})
+
+### IPC Stream
+stream_file <- "files/ex_data.stream"
+
+test_that("Can read the file (parquet)", {
+  # We can read with no error, we assert metadata below
+  expect_error(
+    df <- read_ipc_stream(stream_file),
+    NA
+  )
+})
+
+test_that("Can see the metadata (stream)", {
+  skip_if_version_less_than("2.0.0", "Version 1.0.1 can't read new version metadata.")
+  df <- read_ipc_stream(stream_file)
+
+  expect_s3_class(df, "tbl")
+
+  expect_equal(
+    attributes(df),
+    list(
+      names = letters[1:4],
+      row.names = 1L,
+      top_level = list(
+        field_one = 12,
+        field_two = "more stuff"
+      ),
+      class = c("tbl_df", "tbl", "data.frame")
+    )
+  )
+
+  # column-level attributes
+  expect_equal(attributes(df$a), list(class = "special_string"))
+  expect_equal(
+    attributes(df$c),
+    list(
+      row.names = 1L,
+      names = c("c1", "c2", "c3"),
+      class = c("tbl_df", "tbl", "data.frame")
+    )
+  )
+})
+
+
diff --git a/r/extra-tests/write-files.R b/r/extra-tests/write-files.R
new file mode 100644
index 00000000000..e0927ead4eb
--- /dev/null
+++ b/r/extra-tests/write-files.R
@@ -0,0 +1,39 @@
+# Licensed to the Apache Software Foundation (ASF) under one
+# or more contributor license agreements.  See the NOTICE file
+# distributed with this work for additional information
+# regarding copyright ownership.  The ASF licenses this file
+# to you under the Apache License, Version 2.0 (the
+# "License"); you may not use this file except in compliance
+# with the License.  You may obtain a copy of the License at
+#
+#   http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing,
+# software distributed under the License is distributed on an
+# "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY
+# KIND, either express or implied.  See the License for the
+# specific language governing permissions and limitations
+# under the License.
+
+library(arrow)
+
+if (!dir.exists("extra-tests/files")) {
+  dir.create("extra-tests/files")
+}
+
+source("tests/testthat/helper-data.R")
+
+write_parquet(example_with_metadata, "extra-tests/files/ex_data.parquet")
+
+for (comp in c("lz4", "uncompressed", "zstd")) {
+  if(!codec_is_available(comp)) break
+
+  name <- paste0("extra-tests/files/ex_data_", comp, ".feather")
+  write_feather(example_with_metadata, name, compression = comp)
+}
+
+example_with_metadata_v1 <- example_with_metadata
+example_with_metadata_v1$c <- NULL
+write_feather(example_with_metadata_v1, "extra-tests/files/ex_data_v1.feather", version = 1)
+
+write_ipc_stream(example_with_metadata, "extra-tests/files/ex_data.stream")
diff --git a/r/tests/testthat/golden-files/data-arrow_0.17.0_lz4.feather b/r/tests/testthat/golden-files/data-arrow_0.17.0_lz4.feather
new file mode 100644
index 00000000000..d91acd0cc9e
Binary files /dev/null and b/r/tests/testthat/golden-files/data-arrow_0.17.0_lz4.feather differ
diff --git a/r/tests/testthat/golden-files/data-arrow_0.17.0_uncompressed.feather b/r/tests/testthat/golden-files/data-arrow_0.17.0_uncompressed.feather
new file mode 100644
index 00000000000..0198024ec74
Binary files /dev/null and b/r/tests/testthat/golden-files/data-arrow_0.17.0_uncompressed.feather differ
diff --git a/r/tests/testthat/golden-files/data-arrow_0.17.0_zstd.feather b/r/tests/testthat/golden-files/data-arrow_0.17.0_zstd.feather
new file mode 100644
index 00000000000..f6788231c8a
Binary files /dev/null and b/r/tests/testthat/golden-files/data-arrow_0.17.0_zstd.feather differ
diff --git a/r/tests/testthat/golden-files/data-arrow_1.0.1.parquet b/r/tests/testthat/golden-files/data-arrow_1.0.1.parquet
new file mode 100644
index 00000000000..e1d589bf099
Binary files /dev/null and b/r/tests/testthat/golden-files/data-arrow_1.0.1.parquet differ
diff --git a/r/tests/testthat/golden-files/data-arrow_1.0.1_lz4.feather b/r/tests/testthat/golden-files/data-arrow_1.0.1_lz4.feather
new file mode 100644
index 00000000000..f3a71435a6c
Binary files /dev/null and b/r/tests/testthat/golden-files/data-arrow_1.0.1_lz4.feather differ
diff --git a/r/tests/testthat/golden-files/data-arrow_1.0.1_uncompressed.feather b/r/tests/testthat/golden-files/data-arrow_1.0.1_uncompressed.feather
new file mode 100644
index 00000000000..1188ac66959
Binary files /dev/null and b/r/tests/testthat/golden-files/data-arrow_1.0.1_uncompressed.feather differ
diff --git a/r/tests/testthat/golden-files/data-arrow_1.0.1_zstd.feather b/r/tests/testthat/golden-files/data-arrow_1.0.1_zstd.feather
new file mode 100644
index 00000000000..056b26c1743
Binary files /dev/null and b/r/tests/testthat/golden-files/data-arrow_1.0.1_zstd.feather differ
diff --git a/r/tests/testthat/golden-files/data-arrow_2.0.0.parquet b/r/tests/testthat/golden-files/data-arrow_2.0.0.parquet
new file mode 100644
index 00000000000..6c59115608c
Binary files /dev/null and b/r/tests/testthat/golden-files/data-arrow_2.0.0.parquet differ
diff --git a/r/tests/testthat/golden-files/data-arrow_2.0.0_lz4.feather b/r/tests/testthat/golden-files/data-arrow_2.0.0_lz4.feather
new file mode 100644
index 00000000000..b65da723466
Binary files /dev/null and b/r/tests/testthat/golden-files/data-arrow_2.0.0_lz4.feather differ
diff --git a/r/tests/testthat/golden-files/data-arrow_2.0.0_uncompressed.feather b/r/tests/testthat/golden-files/data-arrow_2.0.0_uncompressed.feather
new file mode 100644
index 00000000000..508903cb49c
Binary files /dev/null and b/r/tests/testthat/golden-files/data-arrow_2.0.0_uncompressed.feather differ
diff --git a/r/tests/testthat/golden-files/data-arrow_2.0.0_zstd.feather b/r/tests/testthat/golden-files/data-arrow_2.0.0_zstd.feather
new file mode 100644
index 00000000000..39c829fda20
Binary files /dev/null and b/r/tests/testthat/golden-files/data-arrow_2.0.0_zstd.feather differ
diff --git a/r/tests/testthat/helper-data.R b/r/tests/testthat/helper-data.R
index a810aa36781..26b1cf0e108 100644
--- a/r/tests/testthat/helper-data.R
+++ b/r/tests/testthat/helper-data.R
@@ -34,12 +34,11 @@ example_with_metadata <- tibble::tibble(
   ),
   d = "four"
 )
-# TODO: collect top-level dataset metadata
-# https://issues.apache.org/jira/browse/ARROW-9271
-# attr(example_with_metadata, "top_level") <- list(
-#   field_one = 12,
-#   field_two = "more stuff"
-# )
+
+attr(example_with_metadata, "top_level") <- list(
+  field_one = 12,
+  field_two = "more stuff"
+)
 
 haven_data <- tibble::tibble(
   num = structure(c(5.1, 4.9),
diff --git a/r/tests/testthat/test-backwards-compatibility.R b/r/tests/testthat/test-backwards-compatibility.R
new file mode 100644
index 00000000000..73c25cdceb7
--- /dev/null
+++ b/r/tests/testthat/test-backwards-compatibility.R
@@ -0,0 +1,100 @@
+# Licensed to the Apache Software Foundation (ASF) under one
+# or more contributor license agreements.  See the NOTICE file
+# distributed with this work for additional information
+# regarding copyright ownership.  The ASF licenses this file
+# to you under the Apache License, Version 2.0 (the
+# "License"); you may not use this file except in compliance
+# with the License.  You may obtain a copy of the License at
+#
+#   http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing,
+# software distributed under the License is distributed on an
+# "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY
+# KIND, either express or implied.  See the License for the
+# specific language governing permissions and limitations
+# under the License.
+
+# To write a new version of a test file for a current version:
+# write_parquet(example_with_metadata, test_path("golden-files/data-arrow_2.0.0.parquet"))
+
+# To write a new version of a test file for an old version, use docker(-compose)
+# to setup a linux distribution and use RStudio's public package manager binary
+# repo to install the old version. The following commands should be run at the
+# root of the arrow repo directory and might need slight adjusments.
+# R_ORG=rstudio R_IMAGE=r-base R_TAG=4.0-focal docker-compose build --no-cache r
+# R_ORG=rstudio R_IMAGE=r-base R_TAG=4.0-focal docker-compose run r /bin/bash
+# R
+# options(repos = "https://packagemanager.rstudio.com/all/__linux__/focal/latest")
+# remotes::install_version("arrow", version = "1.0.1")
+# # get example data into the global env
+# write_parquet(example_with_metadata, "arrow/r/tests/testthat/golden-files/data-arrow_1.0.1.parquet")
+# quit()/exit
+
+expect_identical_with_metadata <- function(object, expected, ..., top_level = TRUE) {
+  attrs_to_keep <- c("names", "class", "row.names")
+  if (!top_level) {
+      # remove not-tbl and not-data.frame attributes
+      for (attribute in names(attributes(expected))) {
+        if (attribute %in% attrs_to_keep) next
+        attributes(expected)[[attribute]] <- NULL
+      }
+  }
+  expect_identical(object, expected, ...)
+}
+
+test_that("reading a known Parquet file to dataframe with 2.0.0", {
+  skip_if_not_available("snappy")
+  pq_file <- test_path("golden-files/data-arrow_2.0.0.parquet")
+
+  df <- read_parquet(pq_file)
+  # this is equivalent to `expect_identical()`
+  expect_identical_with_metadata(df, example_with_metadata)
+})
+
+test_that("reading a known Parquet file to dataframe with 1.0.1", {
+  skip_if_not_available("snappy")
+  pq_file <- test_path("golden-files/data-arrow_1.0.1.parquet")
+
+  df <- read_parquet(pq_file)
+  # 1.0.1 didn't save top-level metadata, so we need to remove it.
+  expect_identical_with_metadata(df, example_with_metadata, top_level = FALSE)
+})
+
+for (comp in c("lz4", "uncompressed", "zstd")) {
+  # write_feather(example_with_metadata, test_path("golden-files/data-arrow_2.0.0_lz4.feather"), compression = "lz4")
+  # write_feather(example_with_metadata, test_path("golden-files/data-arrow_2.0.0_uncompressed.feather"), compression = "uncompressed")
+  # write_feather(example_with_metadata, test_path("golden-files/data-arrow_2.0.0_zstd.feather"), compression = "zstd")
+  test_that("reading a known Feather file to dataframe with 2.0.0", {
+    skip_if_not_available(comp)
+    feather_file <- test_path(paste0("golden-files/data-arrow_2.0.0_", comp,".feather"))
+
+    df <- read_feather(feather_file)
+    expect_identical_with_metadata(df, example_with_metadata)
+  })
+
+  test_that("reading a known Feather file to dataframe with 1.0.1", {
+    skip_if_not_available(comp)
+    feather_file <- test_path(paste0("golden-files/data-arrow_1.0.1_", comp,".feather"))
+
+    df <- read_feather(feather_file)
+    # 1.0.1 didn't save top-level metadata, so we need to remove it.
+    expect_identical_with_metadata(df, example_with_metadata, top_level = FALSE)
+  })
+
+  test_that("reading a known Feather file to dataframe with 0.17.0", {
+    skip_if_not_available(comp)
+    feather_file <- test_path(paste0("golden-files/data-arrow_0.17.0_", comp,".feather"))
+
+    df <- read_feather(feather_file)
+    # the metadata from 0.17.0 doesn't have the top level, the special class is
+    # not maintained and the embedded tibble's attributes are read in a wrong
+    # order. Since this is prior to 1.0.0 punting on checking the attributes
+    # though classes are always checked, so that must be removed before checking.
+    example_with_metadata_sans_special_class <- example_with_metadata
+    example_with_metadata_sans_special_class$a <- unclass(example_with_metadata_sans_special_class$a)
+    expect_equal(df, example_with_metadata_sans_special_class, check.attributes = FALSE)
+  })
+}
+
+# TODO: streams(?)