The easiest way to plan small town day trips from Cleveland is to pick a direction first. Head east and you reach the river towns of Chagrin Falls and Willoughby, with Ashtabula Harbor out on the lake. Go south and you are in the Cuyahoga Valley and the town squares of Hudson and Medina. Go west and you get Olmsted Falls and the lakefront at Vermilion.
Each of the towns below has a walkable historic center and something nearby worth the drive, whether that is a waterfall, a trail or a train. The full historic downtowns guide maps them all, including the ones close enough to the city for an evening.
Hours at small-town shops and restaurants vary, so check the places you want to visit before you set out.
East, south and west
Historic downtowns worth a day
Chagrin Falls
Chagrin Falls
Best for: A waterfall in the middle of town
Chagrin Falls is built around a waterfall on the Chagrin River, with a boardwalk and viewing area steps from Main Street. Walk the shops and restaurants around Triangle Park, browse Fireside Book Shop, then eat on the deck at 17 River Grille above the falls.
The village also puts up holiday lights, which makes it worth a second trip in winter.
Willoughby
Willoughby
Best for: Diners, a bookshop and a castle nearby
Downtown Willoughby is a walkable few blocks along Erie Street in Lake County, with diners, bars and independent shops. Have breakfast at Chagrin River Diner or Kleifeld’s, browse The Viridian Bookshop, then drive to Squire’s Castle in the North Chagrin Reservation to finish the day.
The downtown has nightlife too, so the day can run into the evening before the drive home.
Ashtabula Harbor
Ashtabula Harbor
Best for: A harbor town with a working lift bridge
Ashtabula Harbor’s Bridge Street is a historic row of shops and restaurants near the lift bridge over the Ashtabula River. Walk the street, browse the shops and stay long enough to watch the bridge lift.
It is the longest drive east on this list, out along Lake Erie, so plan a full day. In winter, Lights on the Lake at Lakeshore Park gives you a reason to stay after dark.
Peninsula
Peninsula
Best for: A village inside the national park
Peninsula is a small village inside Cuyahoga Valley National Park, with a short main street along the Cuyahoga River and the Towpath Trail running through town. It is a well-known stop and a natural base for a day in the valley.
Pair a walk through the village with a ride on the Cuyahoga Valley Scenic Railroad, a hike at the Ledges, or produce and pie from Szalay’s Farm.
Hudson
Hudson
Best for: A town green and a clock tower
Hudson’s downtown is a New England style town green with a clock tower, surrounded by older storefronts and the First and Main shopping district. Walk the green, then work through the Main Street shops.
Come back during the holiday season for the outdoor Christkindlmarkt around First and Main. Hudson sits just east of the Cuyahoga Valley, so it pairs well with Peninsula.
Medina
Medina
Best for: A Victorian square with breakfast and a glass of wine
Medina’s downtown is a Victorian era public square with a gazebo and a green, lined with shops, restaurants and taprooms, and it is one of the best known historic downtowns near Cleveland.
Have breakfast at Jane’s Diner on the square, visit Castle Noel, then stop for a glass at Huth & Harris a block away. The square also hosts holiday events, so check what is on before you go.
Olmsted Falls
Olmsted Falls
Best for: Antiques and boutiques close to the city
Downtown Olmsted Falls is a small historic shopping district of older buildings along Columbia Road near the railroad tracks, and it is one of the closer historic downtowns on the west side.
Spend an afternoon in the boutiques and antique shops, including Second Thyme Around and Treasure House of the Falls. Berea is a short drive east if you want to add the Berea Falls overlook.
Vermilion
Vermilion
Best for: A lakefront town for a summer day
Vermilion sits where the Vermilion River meets Lake Erie, with a small downtown of shops and restaurants a short walk from the lake.
Grab breakfast downtown, walk to the water, then drive out to Paper Moon Vineyards or the trails at Mill Hollow. It is a boat town and a summer trip first, so save it for warm weather.
Two towns, one day
Pairings that make the drive worth it
Some of these towns sit close enough together to combine. Peninsula and Hudson work as a pair: a morning on the Towpath Trail or the scenic railroad in the valley, then the afternoon on the Hudson green. Chagrin Falls and Willoughby both sit east of the city, so breakfast on Erie Street and a late lunch above the falls is a manageable loop.
On the west side, Olmsted Falls pairs with Berea, whose downtown sits on a triangle of streets next to the Baldwin Wallace campus with The Cornerstone Brewing Company on the triangle. Further south, Medina pairs with Wadsworth, where the Main Street of older storefronts ends the day well if the Celestia Theater has an evening show.
Longer drives
When you have a full day to spare
Sandusky, farther west past Vermilion, works best as an add-on to a Cedar Point day, with older stone buildings, Washington Park and a waterfront on Sandusky Bay. Walk the downtown and waterfront, then drive out to Firelands Winery.
Kent, to the southeast next to the Kent State campus and the Cuyahoga River, has a compact grid of restaurants, bars and small shops that suits an afternoon of shopping followed by dinner. Both are on the map in the full list of historic downtowns near Cleveland.
Good to know
Questions before you go.
Which historic downtown is closest to Cleveland?
Bedford and Rocky River are both close to the city. Bedford has a small commons on Broadway Avenue and a walk to the Great Falls of Tinker’s Creek in Viaduct Park, and Rocky River’s shops, bakeries and wine bars line Detroit Road and Old Detroit Road just west of the city.
Which of these towns are worth visiting in winter?
Hudson for its outdoor Christkindlmarkt, Ashtabula Harbor for Lights on the Lake, and Bedford and Berea for their holiday lights. Chagrin Falls puts up holiday lights too, and Medina’s square hosts holiday events.
Plan the next trip
See every historic downtown near Cleveland
The full guide maps walkable town centers, main streets and public squares across Northeast Ohio, with what to do in each one.