diff --git a/.changeset/new-taxis-stare.md b/.changeset/new-taxis-stare.md
new file mode 100644
index 0000000000..b3085a58cd
--- /dev/null
+++ b/.changeset/new-taxis-stare.md
@@ -0,0 +1,34 @@
+---
+"react-router": minor
+"@remix-run/router": minor
+---
+
+Allows optional routes and optional static segments
+
+**Optional params examples**
+
+`:lang?/about` will get expanded matched with
+
+```
+/:lang/about
+/about
+```
+
+`/multistep/:widget1?/widget2?/widget3?`
+Will get expanded matched with:
+
+```
+/multistep
+/multistep/:widget1
+/multistep/:widget1/:widget2
+/multistep/:widget1/:widget2/:widget3
+```
+
+**optional static segment example**
+
+`/fr?/about` will get expanded and matched with:
+
+```
+/about
+/fr/about
+```
diff --git a/contributors.yml b/contributors.yml
index aa40f67154..091718e2c1 100644
--- a/contributors.yml
+++ b/contributors.yml
@@ -76,6 +76,7 @@
 - KostiantynPopovych
 - KutnerUri
 - latin-1
+- lordofthecactus
 - liuhanqu
 - loun4
 - lqze
diff --git a/package.json b/package.json
index d359a2a285..d7b6afc2db 100644
--- a/package.json
+++ b/package.json
@@ -107,7 +107,7 @@
   },
   "filesize": {
     "packages/router/dist/router.umd.min.js": {
-      "none": "35 kB"
+      "none": "35.5 kB"
     },
     "packages/react-router/dist/react-router.production.min.js": {
       "none": "12.5 kB"
diff --git a/packages/react-router/__tests__/path-matching-test.tsx b/packages/react-router/__tests__/path-matching-test.tsx
index dd5e58a3af..4f4a4ad32e 100644
--- a/packages/react-router/__tests__/path-matching-test.tsx
+++ b/packages/react-router/__tests__/path-matching-test.tsx
@@ -6,6 +6,14 @@ function pickPaths(routes: RouteObject[], pathname: string): string[] | null {
   return matches && matches.map((match) => match.route.path || "");
 }
 
+function pickPathsAndParams(routes: RouteObject[], pathname: string) {
+  let matches = matchRoutes(routes, pathname);
+  return (
+    matches &&
+    matches.map((match) => ({ path: match.route.path, params: match.params }))
+  );
+}
+
 describe("path matching", () => {
   test("root vs. dynamic", () => {
     let routes = [{ path: "/" }, { path: ":id" }];
@@ -251,20 +259,184 @@ describe("path matching with splats", () => {
 
     expect(match).not.toBeNull();
     expect(match).toHaveLength(3);
-    expect(match[0]).toMatchObject({
+    expect(match![0]).toMatchObject({
       params: { "*": "abc" },
       pathname: "/",
       pathnameBase: "/",
     });
-    expect(match[1]).toMatchObject({
+    expect(match![1]).toMatchObject({
       params: { "*": "abc" },
       pathname: "/courses",
       pathnameBase: "/courses",
     });
-    expect(match[2]).toMatchObject({
+    expect(match![2]).toMatchObject({
       params: { "*": "abc" },
       pathname: "/courses/abc",
       pathnameBase: "/courses",
     });
   });
 });
+
+describe("path matchine with optional segments", () => {
+  test("optional static segment at the start of the path", () => {
+    let routes = [
+      {
+        path: "/en?/abc",
+      },
+    ];
+
+    expect(pickPathsAndParams(routes, "/")).toEqual(null);
+    expect(pickPathsAndParams(routes, "/abc")).toEqual([
+      {
+        path: "/en?/abc",
+        params: {},
+      },
+    ]);
+    expect(pickPathsAndParams(routes, "/en/abc")).toEqual([
+      {
+        path: "/en?/abc",
+        params: {},
+      },
+    ]);
+    expect(pickPathsAndParams(routes, "/en/abc/bar")).toEqual(null);
+  });
+
+  test("optional static segment at the end of the path", () => {
+    let routes = [
+      {
+        path: "/nested/one?/two?",
+      },
+    ];
+
+    expect(pickPathsAndParams(routes, "/nested")).toEqual([
+      {
+        path: "/nested/one?/two?",
+        params: {},
+      },
+    ]);
+    expect(pickPathsAndParams(routes, "/nested/one")).toEqual([
+      {
+        path: "/nested/one?/two?",
+        params: {},
+      },
+    ]);
+    expect(pickPathsAndParams(routes, "/nested/one/two")).toEqual([
+      {
+        path: "/nested/one?/two?",
+        params: {},
+      },
+    ]);
+    expect(pickPathsAndParams(routes, "/nested/one/two/baz")).toEqual(null);
+  });
+
+  test("intercalated optional static segments", () => {
+    let routes = [
+      {
+        path: "/nested/one?/two/three?",
+      },
+    ];
+
+    expect(pickPathsAndParams(routes, "/nested")).toEqual(null);
+    expect(pickPathsAndParams(routes, "/nested/one")).toEqual(null);
+    expect(pickPathsAndParams(routes, "/nested/two")).toEqual([
+      {
+        path: "/nested/one?/two/three?",
+        params: {},
+      },
+    ]);
+    expect(pickPathsAndParams(routes, "/nested/one/two")).toEqual([
+      {
+        path: "/nested/one?/two/three?",
+        params: {},
+      },
+    ]);
+    expect(pickPathsAndParams(routes, "/nested/one/two/three")).toEqual([
+      {
+        path: "/nested/one?/two/three?",
+        params: {},
+      },
+    ]);
+  });
+});
+
+describe("path matching with optional dynamic segments", () => {
+  test("optional params at the start of the path", () => {
+    let routes = [
+      {
+        path: "/:lang?/abc",
+      },
+    ];
+
+    expect(pickPathsAndParams(routes, "/")).toEqual(null);
+    expect(pickPathsAndParams(routes, "/abc")).toEqual([
+      {
+        path: "/:lang?/abc",
+        params: {},
+      },
+    ]);
+    expect(pickPathsAndParams(routes, "/en/abc")).toEqual([
+      {
+        path: "/:lang?/abc",
+        params: { lang: "en" },
+      },
+    ]);
+    expect(pickPathsAndParams(routes, "/en/abc/bar")).toEqual(null);
+  });
+
+  test("optional params at the end of the path", () => {
+    let routes = [
+      {
+        path: "/nested/:one?/:two?",
+      },
+    ];
+
+    expect(pickPathsAndParams(routes, "/nested")).toEqual([
+      {
+        path: "/nested/:one?/:two?",
+        params: {},
+      },
+    ]);
+    expect(pickPathsAndParams(routes, "/nested/foo")).toEqual([
+      {
+        path: "/nested/:one?/:two?",
+        params: { one: "foo" },
+      },
+    ]);
+    expect(pickPathsAndParams(routes, "/nested/foo/bar")).toEqual([
+      {
+        path: "/nested/:one?/:two?",
+        params: { one: "foo", two: "bar" },
+      },
+    ]);
+    expect(pickPathsAndParams(routes, "/nested/foo/bar/baz")).toEqual(null);
+  });
+
+  test("intercalated optional params", () => {
+    let routes = [
+      {
+        path: "/nested/:one?/two/:three?",
+      },
+    ];
+
+    expect(pickPathsAndParams(routes, "/nested")).toEqual(null);
+    expect(pickPathsAndParams(routes, "/nested/foo")).toEqual(null);
+    expect(pickPathsAndParams(routes, "/nested/two")).toEqual([
+      {
+        path: "/nested/:one?/two/:three?",
+        params: {},
+      },
+    ]);
+    expect(pickPathsAndParams(routes, "/nested/foo/two")).toEqual([
+      {
+        path: "/nested/:one?/two/:three?",
+        params: { one: "foo" },
+      },
+    ]);
+    expect(pickPathsAndParams(routes, "/nested/foo/two/bar")).toEqual([
+      {
+        path: "/nested/:one?/two/:three?",
+        params: { one: "foo", three: "bar" },
+      },
+    ]);
+  });
+});
diff --git a/packages/router/utils.ts b/packages/router/utils.ts
index d9ce7d3242..72699b4ee1 100644
--- a/packages/router/utils.ts
+++ b/packages/router/utils.ts
@@ -415,7 +415,43 @@ function flattenRoutes<
       return;
     }
 
-    branches.push({ path, score: computeScore(path, route.index), routesMeta });
+    // Handle optional params - /path/:optional?
+    let segments = path.split("/");
+    let optionalParams: string[] = [];
+    segments.forEach((segment) => {
+      let match = segment.match(/^:?([^?]+)\?$/);
+      if (match) {
+        optionalParams.push(match[1]);
+      }
+    });
+
+    if (optionalParams.length > 0) {
+      for (let i = 0; i <= optionalParams.length; i++) {
+        let newPath = path;
+        let newMeta = routesMeta.map((m) => ({ ...m }));
+
+        for (let j = optionalParams.length - 1; j >= 0; j--) {
+          let re = new RegExp(`(\\/:?${optionalParams[j]})\\?`);
+          let replacement = j < i ? "$1" : "";
+          newPath = newPath.replace(re, replacement);
+          newMeta[newMeta.length - 1].relativePath = newMeta[
+            newMeta.length - 1
+          ].relativePath.replace(re, replacement);
+        }
+
+        branches.push({
+          path: newPath,
+          score: computeScore(newPath, route.index),
+          routesMeta: newMeta,
+        });
+      }
+    } else {
+      branches.push({
+        path,
+        score: computeScore(path, route.index),
+        routesMeta,
+      });
+    }
   });
 
   return branches;