diff --git a/packages/aws-cdk/lib/util/npm.ts b/packages/aws-cdk/lib/util/npm.ts
new file mode 100644
index 0000000000000..c46167342a5a8
--- /dev/null
+++ b/packages/aws-cdk/lib/util/npm.ts
@@ -0,0 +1,19 @@
+import { exec as _exec } from 'child_process';
+import { promisify } from 'util';
+import * as semver from 'semver';
+import { debug } from '../../lib/logging';
+
+const exec = promisify(_exec);
+
+export async function getLatestVersionFromNpm(): Promise<string> {
+  const { stdout, stderr } = await exec('npm view aws-cdk version');
+  if (stderr && stderr.trim().length > 0) {
+    debug(`The 'npm view' command generated an error stream with content [${stderr.trim()}]`);
+  }
+  const latestVersion = stdout.trim();
+  if (!semver.valid(latestVersion)) {
+    throw new Error(`npm returned an invalid semver ${latestVersion}`);
+  }
+
+  return latestVersion;
+}
diff --git a/packages/aws-cdk/lib/version.ts b/packages/aws-cdk/lib/version.ts
index e407935ce2bfa..01cfbe0dae463 100644
--- a/packages/aws-cdk/lib/version.ts
+++ b/packages/aws-cdk/lib/version.ts
@@ -1,16 +1,17 @@
-import { exec as _exec } from 'child_process';
 import * as path from 'path';
-import { promisify } from 'util';
 import * as colors from 'colors/safe';
 import * as fs from 'fs-extra';
 import * as semver from 'semver';
 import { debug, print } from '../lib/logging';
 import { formatAsBanner } from '../lib/util/console-formatters';
 import { cdkCacheDir } from './util/directories';
+import { getLatestVersionFromNpm } from './util/npm';
 
 const ONE_DAY_IN_SECONDS = 1 * 24 * 60 * 60;
 
-const exec = promisify(_exec);
+const UPGRADE_DOCUMENTATION_LINKS: Record<number, string> = {
+  1: 'https://docs.aws.amazon.com/cdk/v2/guide/migrating-v2.html',
+};
 
 export const DISPLAY_VERSION = `${versionNumber()} (build ${commit()})`;
 
@@ -79,14 +80,7 @@ export async function latestVersionIfHigher(currentVersion: string, cacheFile: V
     return null;
   }
 
-  const { stdout, stderr } = await exec('npm view aws-cdk version');
-  if (stderr && stderr.trim().length > 0) {
-    debug(`The 'npm view' command generated an error stream with content [${stderr.trim()}]`);
-  }
-  const latestVersion = stdout.trim();
-  if (!semver.valid(latestVersion)) {
-    throw new Error(`npm returned an invalid semver ${latestVersion}`);
-  }
+  const latestVersion = await getLatestVersionFromNpm();
   const isNewer = semver.gt(latestVersion, currentVersion);
   await cacheFile.update(latestVersion);
 
@@ -97,19 +91,30 @@ export async function latestVersionIfHigher(currentVersion: string, cacheFile: V
   }
 }
 
-export async function displayVersionMessage(): Promise<void> {
+function getMajorVersionUpgradeMessage(currentVersion: string): string | void {
+  const currentMajorVersion = semver.major(currentVersion);
+  if (UPGRADE_DOCUMENTATION_LINKS[currentMajorVersion]) {
+    return `Information about upgrading from version ${currentMajorVersion}.x to version ${currentMajorVersion + 1}.x is available here: ${UPGRADE_DOCUMENTATION_LINKS[currentMajorVersion]}`;
+  }
+}
+
+function getVersionMessage(currentVersion: string, laterVersion: string): string[] {
+  return [
+    `Newer version of CDK is available [${colors.green(laterVersion as string)}]`,
+    getMajorVersionUpgradeMessage(currentVersion),
+    'Upgrade recommended (npm install -g aws-cdk)',
+  ].filter(Boolean) as string[];
+}
+
+export async function displayVersionMessage(currentVersion = versionNumber(), versionCheckCache?: VersionCheckTTL): Promise<void> {
   if (!process.stdout.isTTY || process.env.CDK_DISABLE_VERSION_CHECK) {
     return;
   }
 
   try {
-    const versionCheckCache = new VersionCheckTTL();
-    const laterVersion = await latestVersionIfHigher(versionNumber(), versionCheckCache);
+    const laterVersion = await latestVersionIfHigher(currentVersion, versionCheckCache ?? new VersionCheckTTL());
     if (laterVersion) {
-      const bannerMsg = formatAsBanner([
-        `Newer version of CDK is available [${colors.green(laterVersion as string)}]`,
-        'Upgrade recommended (npm install -g aws-cdk)',
-      ]);
+      const bannerMsg = formatAsBanner(getVersionMessage(currentVersion, laterVersion));
       bannerMsg.forEach((e) => print(e));
     }
   } catch (err) {
diff --git a/packages/aws-cdk/test/version.test.ts b/packages/aws-cdk/test/version.test.ts
index 01b120c463a6b..9019de161d159 100644
--- a/packages/aws-cdk/test/version.test.ts
+++ b/packages/aws-cdk/test/version.test.ts
@@ -4,6 +4,7 @@ import { promisify } from 'util';
 import * as fs from 'fs-extra';
 import * as sinon from 'sinon';
 import * as logging from '../lib/logging';
+import * as npm from '../lib/util/npm';
 import { latestVersionIfHigher, VersionCheckTTL, displayVersionMessage } from '../lib/version';
 
 jest.setTimeout(10_000);
@@ -77,9 +78,61 @@ test('No Version specified for storage in the TTL file', async () => {
 });
 
 test('Skip version check if environment variable is set', async () => {
-  process.stdout.isTTY = true;
-  process.env.CDK_DISABLE_VERSION_CHECK = '1';
+  sinon.stub(process, 'stdout').value({ ...process.stdout, isTTY: true });
+  sinon.stub(process, 'env').value({ ...process.env, CDK_DISABLE_VERSION_CHECK: '1' });
   const printStub = sinon.stub(logging, 'print');
   await displayVersionMessage();
   expect(printStub.called).toEqual(false);
 });
+
+describe('version message', () => {
+  let previousIsTty: true | undefined;
+  beforeAll(() => {
+    previousIsTty = process.stdout.isTTY;
+    process.stdout.isTTY = true;
+  });
+
+  afterAll(() => {
+    process.stdout.isTTY = previousIsTty;
+  });
+
+  test('Prints a message when a new version is available', async () => {
+    // Given the current version is 1.0.0 and the latest version is 1.1.0
+    const currentVersion = '1.0.0';
+    jest.spyOn(npm, 'getLatestVersionFromNpm').mockResolvedValue('1.1.0');
+    const printSpy = jest.spyOn(logging, 'print');
+
+    // When displayVersionMessage is called
+    await displayVersionMessage(currentVersion, new VersionCheckTTL(tmpfile(), 0));
+
+    // Then the new version message is printed to stdout
+    expect(printSpy).toHaveBeenCalledWith(expect.stringContaining('1.1.0'));
+  });
+
+  test('Includes major upgrade documentation when available', async() => {
+    // Given the current version is 1.0.0 and the latest version is 2.0.0
+    const currentVersion = '1.0.0';
+    jest.spyOn(npm, 'getLatestVersionFromNpm').mockResolvedValue('2.0.0');
+    const printSpy = jest.spyOn(logging, 'print');
+
+    // When displayVersionMessage is called
+    await displayVersionMessage(currentVersion, new VersionCheckTTL(tmpfile(), 0));
+
+    // Then the V1 -> V2 documentation is printed
+    expect(printSpy).toHaveBeenCalledWith(expect.stringContaining('Information about upgrading from version 1.x to version 2.x is available here: https://docs.aws.amazon.com/cdk/v2/guide/migrating-v2.html'));
+  });
+
+  test('Does not include major upgrade documentation when unavailable', async() => {
+    // Given current version is 99.0.0 and the latest version is 100.0.0
+    const currentVersion = '99.0.0';
+    jest.spyOn(npm, 'getLatestVersionFromNpm').mockResolvedValue('100.0.0');
+    const printSpy = jest.spyOn(logging, 'print');
+
+    // When displayVersionMessage is called
+    await displayVersionMessage(currentVersion, new VersionCheckTTL(tmpfile(), 0));
+
+    // Then no upgrade documentation is printed
+    expect(printSpy).toHaveBeenCalledWith(expect.stringContaining('100.0.0'));
+    expect(printSpy).not.toHaveBeenCalledWith(expect.stringContaining('Information about upgrading from 99.x to 100.x'));
+  });
+});