5 Best Small Towns to Visit in the Fall

Even with a pandemic, fall is still a time for apple picking and cider, leaf peeping and sweaters. And nothing puts you more in the fall spirit than a road trip to a small town where you can amble down its brightly colored tree-lined streets with a cup of hot coffee in hand. This list is by no means exhaustive, but here are 5 of my favorite small towns to visit in the fall. What are yours?

1. Lake Forest, Illinois

small town in fall--lake forest market square

It’s hard to start this list without mentioning the small town I’ve chosen to call home. Lake Forest is nestled along the shore of Lake Michigan about an hour north of Chicago. With its historic Howard Van Doren Shaw designed Market Square, quaint little shops, rambling ravines, and elegant country estates, you will not run out of sights to see. Stay at The Deerpath Inn, a sophisticated country inn recently named #18 in the world by Travel + Leisure. Dine in the town square at Market House. Walk or bike through the Middlefork Savanna and Fort Sheridan Forest Preserve to enjoy lake, forest, and grassland views. And, before you go, don’t forget to swing by Amedei Mercatino, Lake Forest’s in town open air market, to buy your pumpkin.

fall farmer's market in lake forest--best small towns
lake forest beach in fall

2. Woodstock, Vermont

woodstock vermont-best small town in America

Named “the most beautiful town in America” by The Traveler Magazine, Woodstock lives up to its hype. There is no better small town to visit in the fall for leaf-peeping than this rural enclave in the heart of the Green Mountains. Stay at The Woodstock Inn where you are within walking distance to the village shops and restaurants. Visit Billings Farm, established in 1871, to experience Vermont’s farming history. Take cooking classes at King Arthur Baking Company. And make sure you dine at Simon Pearce’s fabulous restaurant located in their glassblowing factory above a dam in Queechee.

woodstock vermont cows in fall--best small towns

3. Bedford, New York

small town Connecticut in fall

This quaint little town is located in Westchester County, New York, very close to the Connecticut border. Bedford is also the village that Martha Stewart calls home. This is another New England small town that makes a perfect fall destination to see multi-colored foliage and charming little shops. Stay at The Bedford Post Inn (owned by Richard Gere). Catch a show at The Bedford Playhouse. Finally, indulge in a delicious traditional French dinner at Michelin Guide’s La Cremaillere. And visit nearby Greenwich, Connecticut while you are there.

village road in fall--best small towns

4. Sutton’s Bay, Michigan

small towns restaurant in fall on lake

Just 12 miles from Traverse City lies rolling farmland, sandy beaches, wine country, and quaint villages all along the shore of Lake Michigan. Stay at the Inn at Black Star Farms, a 160 acre estate nestled nestled below a hillside of vineyards with sweeping pastoral views. Do wine tastings and village strolls. Dine at The Riverside Inn in nearby Leland.

5. Bar Harbor, Maine

Acadia National Park in Fall best small towns

Bar Harbor is the gateway to Acadia National Park, and is often noted as being one of America’s Favorite Small Towns. About 160 miles from Portland, the park is 47,000 acres on Mount Desert Island and one of the most majestic places you can visit. It also comes with activities for everyone. From fall foliage viewing, winter skiing, spring fishing or summer hikes, this is a small town just about anyone can enjoy. Stay at Balance Rock Inn. Dine at The Travelin Lobster. And whatever you do, don’t miss a stroll through town and Acadia National Park.

lobster shack in Maine best small towns

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