Rebecca Engel
A great weekend away doesn’t need a long flight or a big city. It needs a place small enough to walk, old enough to have some stories, and good enough that Sunday afternoon comes way too fast.
These are 25 charming weekend getaway ideas across the US, ordered by region from New England to the Pacific Northwest, so it’s easy to find one within reach. Each one comes with the nearest big city, what to do once you’re there, and the best time to go.
1. Woodstock, Vermont
Woodstock looks like the Vermont village on a postcard, with a village green, white steeples and a covered bridge right in the middle of town. It’s about two and a half hours from Boston and an hour and a half from Burlington.
Walk across the Middle Covered Bridge, then spend an afternoon at Billings Farm and Museum, a working dairy farm that dates to 1871. Next door, Marsh-Billings-Rockefeller National Historical Park is the only national park focused on the story of conservation, with old carriage roads winding through the woods.
Late September to mid October brings the foliage and the biggest crowds. If you want more of the same scenery, this guide to covered bridges in Vermont makes a good drive for Saturday afternoon.
2. Kennebunkport, Maine
Kennebunkport is a classic Maine harbor town about an hour and a half from Boston. Dock Square sits right on the Kennebunk River, packed with shops, galleries and lobster rolls.
Drive Ocean Avenue past the big shingled summer houses to Walker’s Point, the Bush family’s summer compound, which you can see from the road. For something different, the Seashore Trolley Museum calls itself the oldest and largest electric railway museum in the world.
June to mid October is the season, and July and August get busy. Portland is only 35 minutes up the road if you want to add a city night, and this list of things to do in Portland, Maine has plenty for it.
3. Mystic, Connecticut
Mystic isn’t technically a town at all. It’s a village split between Groton and Stonington, sitting about two hours from Boston, two and a half from New York City and an hour from Providence.
The Mystic Seaport Museum is the main event. Its star is the Charles W. Morgan, built in 1841, the last wooden whaleship in the world and the oldest commercial ship still afloat in the US.
Downtown, the 1922 drawbridge still lifts for passing boats, and Mystic Pizza is the pizzeria that gave the 1988 movie its name. The aquarium, with its beluga whales, is a good rainy day backup.
4. Newport, Rhode Island
Newport is where the richest families of the Gilded Age built their summer “cottages,” which turned out to be mansions. It’s about an hour and a half from Boston and three and a half hours from New York City.
Tour The Breakers, the Vanderbilt house finished in 1895, then walk the Cliff Walk along the ocean behind the mansions. Ocean Drive is a beautiful ten mile loop around the rocky south end of the island.
In town, Touro Synagogue, built in 1763, is the oldest surviving synagogue building in the country. May through October is the best time for a weekend, and the mansions dress up for Christmas in December.
5. Cape May, New Jersey
The whole town of Cape May is a National Historic Landmark, thanks to one of the best collections of Victorian houses in the country. It’s about an hour and a half to two hours from Philadelphia and two and a half to three from New York City.
Stroll the gingerbread trimmed streets, then tour the Emlen Physick Estate, an 1879 mansion designed by Frank Furness. Climb the 199 steps of the Cape May Lighthouse for a view of where Delaware Bay meets the Atlantic.
Late May through October is beach season, and September is the sweet spot. The Cape May Lewes Ferry to Delaware makes an easy add on if you want to see both sides of the bay.
6. Hudson, New York
Hudson is one of the easiest car free weekends from New York City. Amtrak gets there from Penn Station in about two hours and drops you downtown, a short walk from everything.
Warren Street is the heart of it, a long stretch of antique shops, design stores and very good restaurants. Just outside town, Olana was the home of painter Frederic Church, a Persian style house set on a hill with sweeping views of the Hudson River, and its grounds are free to wander.
Across the river in Catskill, the Thomas Cole National Historic Site shows where the Hudson River School of painting began. Late September and October are the prettiest time to go.
7. Annapolis, Maryland
Annapolis is a sailing town with a lot of history, about 45 minutes from Washington, DC and 35 minutes from Baltimore. The brick streets run downhill from the State House to the water.
The Maryland State House, finished in 1772, is the oldest state capitol still in continuous legislative use, and it’s where the Treaty of Paris was ratified in 1784. The US Naval Academy sits right next to downtown, but check the visitor access rules before you go, since they require ID and can change.
Grab a sandwich at Chick and Ruth’s Delly, a Main Street institution since 1965. April through October is the best stretch, and October brings the big sailboat and powerboat shows.
8. Old Town Alexandria, Virginia
Old Town Alexandria is only 15 or 20 minutes from Washington, DC, and you can get there on the Metro. It feels like a different century once you’re walking its brick sidewalks.
A free trolley runs down King Street to the waterfront. The Torpedo Factory Art Center is a real torpedo plant from 1918 that’s been full of artists’ studios since 1974, and Gadsby’s Tavern and Carlyle House show what the town looked like in George Washington’s day.
The tower of the George Washington Masonic National Memorial looks down over it all from Shooter’s Hill. If you want to stretch your legs, Mount Vernon is about eight miles away along the Mount Vernon Trail.
9. Charlottesville, Virginia
Charlottesville is about two hours from Washington, DC and an hour and a quarter from Richmond. It’s a college town with Blue Ridge views and a lot of Thomas Jefferson.
Monticello, Jefferson’s home on a mountaintop outside town, and the University of Virginia’s original Academical Village, with its Rotunda, are a UNESCO World Heritage Site together. Back in town, the Downtown Mall is a brick pedestrian street lined with restaurants and shops.
The wineries along the Monticello Wine Trail fill a Saturday easily, and Skyline Drive in Shenandoah National Park is about 40 minutes away. October and spring are ideal, but book early for graduation or a home football weekend.
10. Savannah, Georgia
Savannah might be the most charming city in the South. It’s laid out around 22 leafy squares, shaded by live oaks dripping with Spanish moss, and it’s about two hours from Charleston and four from Atlanta.
Walk from square to square down to Forsyth Park and its 1858 fountain. Bonaventure Cemetery, just outside downtown, is one of the most beautiful and eerie places in Georgia.
Get in line at Leopold’s Ice Cream, open since 1919. March and April bring the azaleas, and St. Patrick’s Day is one of the biggest parties of the year. This list of things to do in Savannah covers much more.
11. St. Augustine, Florida
St. Augustine is the oldest continuously settled European city in the continental US, about 45 minutes from Jacksonville and under two hours from Orlando. Its old town feels more like Spain than Florida.
The Castillo de San Marcos, begun in 1672, is the oldest masonry fort in the continental US, built from coquina, a stone made of crushed shells. Flagler College fills the old Ponce de León Hotel from 1888, and its Tiffany glass is worth the tour.
Walk car free St. George Street, then climb the 219 steps of the St. Augustine Lighthouse. October through April is the best time to go, and the Nights of Lights display makes the holidays especially pretty.
12. Beaufort, South Carolina
Beaufort, pronounced BYOO fert, is a quiet Lowcountry town about an hour from Savannah and an hour and a half from Charleston. Its streets are lined with antebellum homes and huge oaks.
The Point neighborhood has starred in movies like The Big Chill and Forrest Gump, and Henry C. Chambers Waterfront Park is the place to watch the sunset over the river. On nearby St. Helena Island, the Penn Center was founded in 1862 as one of the first schools for freed people.
Keep driving out to Hunting Island State Park for a wild, empty beach. Spring and fall are best, since summer here is hot, humid and buggy.
13. Franklin, Tennessee
Franklin is only about 30 minutes south of Nashville, but it feels like a small town from another time. Its Main Street is lined with brick storefronts, bookstores and cafes.
The Franklin Theatre opened in 1937 and still shows movies and concerts after a careful restoration. Carnton, built in 1826, became a field hospital after the Battle of Franklin in 1864, and its tour is one of the most moving Civil War stops in the South.
The tiny village of Leiper’s Fork is about 15 minutes away, with galleries and live music. Spring and October are the best time to go, and Dickens of a Christmas takes over downtown in December.
14. Eureka Springs, Arkansas
Eureka Springs is a Victorian spa town tucked into the Ozark hills, about an hour from Fayetteville and two and a half hours from Tulsa. Its streets twist up and down the hillsides, and the whole downtown is on the National Register of Historic Places.
The 1886 Crescent Hotel sits above town and calls itself America’s most haunted hotel. Thorncrown Chapel, a glass chapel in the woods designed by E. Fay Jones, has 425 windows and is one of the most beautiful buildings in the country.
The old one lane Beaver Bridge is a short drive from town. April and May bring the dogwoods, and October brings the fall color.
15. Fredericksburg, Texas
Fredericksburg is the heart of the Texas Hill Country, about an hour and a quarter from San Antonio and an hour and a half from Austin. It was founded by German settlers, and that heritage still shows on Main Street.
The National Museum of the Pacific War is built around the old hotel in Admiral Nimitz’s hometown. About 18 miles north, Enchanted Rock is a pink granite dome that rises 425 feet, and weekend day passes should be reserved ahead.
Wineries line the highway out of town. Spring brings the bluebonnets, and summer means peach season. See more German towns in Texas if you want to keep going.
16. Galena, Illinois
Galena is a 19th century river town about three hours from Chicago and 20 minutes from Dubuque, Iowa. Most of the town is a National Register historic district, and it looks it.
Main Street is a long curve of brick storefronts full of shops, wine rooms and restaurants. The Ulysses S. Grant Home was given to Grant by local citizens in 1865, but its hours are limited, so check before you go.
Walk the Galena River Trail, or head out to the hills for a view over the valley. Late September and October are the prettiest weeks of the year here.
17. Mackinac Island, Michigan
Cars have been banned on Mackinac Island since 1898, so you get around by bike, on foot or by horse drawn carriage. Ferries from Mackinaw City and St. Ignace take about 20 minutes, and Mackinaw City is around four hours from Detroit.
Rent a bike and ride the eight mile loop around the island on M-185, a state highway with no cars at all. The Grand Hotel, opened in 1887, has a front porch about 660 feet long.
Climb up to Fort Mackinac and Arch Rock, then pick up fudge on Main Street like everyone else. Late May to October is the season, and the Lilac Festival fills the island in June.
18. Saugatuck, Michigan
Saugatuck is a small art town on Lake Michigan, about two and a half hours from Chicago and 45 minutes from Grand Rapids. Keep in mind you lose an hour crossing into Eastern time.
The town’s chain ferry is the last hand cranked chain ferry in the US, and it has crossed the Kalamazoo River for well over a century. On the other side, climb the 300 plus steps up Mount Baldhead, then walk down to Oval Beach.
Saugatuck Dunes State Park has quieter trails through the dunes to the lake. June through September is for the beach, and fall is calmer and very pretty.
19. Stillwater, Minnesota
Stillwater calls itself the Birthplace of Minnesota, and it’s about 30 minutes from St. Paul and 40 from Minneapolis. Its Main Street runs along the St. Croix River, full of antique shops and bookstores.
The 1931 Lift Bridge no longer carries cars and is open to walkers and cyclists as part of a 4.7 mile loop trail into Wisconsin. Paddleboat cruises head out on the river in the warmer months.
Late September to mid October is when the river valley turns orange and red. Summer is all about being on the water.
20. Ouray, Colorado
Ouray calls itself the Switzerland of America, and it earns the name with steep mountain walls on every side. It’s about 40 minutes from the airport in Montrose, which makes flying in the easiest way to fit it into a weekend.
Soak in the Ouray Hot Springs Pool, where the water runs from about 77 to 106 degrees. Box Cañon Falls roars through a narrow slot canyon right at the edge of town.
The Million Dollar Highway climbs 23 miles over Red Mountain Pass to Silverton, but check road conditions first, since slides can close it. Mid June to early October is the best time, and winter brings ice climbing.
21. Park City, Utah
Park City is an old silver mining town turned mountain resort, only about 40 minutes from the Salt Lake City airport. That makes it one of the easiest mountain weekends in the West.
Historic Main Street is lined with restaurants, galleries and the Egyptian Theatre, which opened on Christmas Day in 1926. Utah Olympic Park still has the ski jumps from the 2002 Winter Olympics.
Winter is ski season, and Park City Mountain is one of the largest ski resorts in the country. Summer trades the snow for hiking and mountain biking on the same slopes.
22. Bisbee, Arizona
Bisbee is a former copper mining town built into a canyon, about an hour and a half from Tucson. At around 5,300 feet, it stays cooler than the desert below.
Ride a mine train deep underground on the Queen Mine Tour, then wander Brewery Gulch and the stair streets that climb between the houses. The Copper Queen Hotel has been open since 1902.
Stop at the edge of the Lavender Pit for a look at the huge old mine. Spring and fall are the best times to go, and the Bisbee 1000 stair climb takes over town in October.
23. Carmel-by-the-Sea, California
Carmel-by-the-Sea is a tiny storybook town on the coast, about two hours from San Francisco. It’s famous for its fairy tale cottages, built by Hugh Comstock in the 1920s, and for having no street addresses at all.
Walk down to Carmel Beach, where dogs are allowed off leash, then visit Mission San Carlos Borromeo de Carmelo, founded in 1771. Point Lobos, three miles south, has some of the most beautiful coastline in California.
September and October bring the clearest weather, since summer is often foggy. This list of things to do in Carmel-by-the-Sea has plenty more.
24. Healdsburg, California
Healdsburg is a Sonoma County wine town about an hour and a half from San Francisco. It’s laid out around a leafy plaza from the 1850s, with tasting rooms and restaurants on every side.
Head out to Dry Creek Valley for its Zinfandel, or rent a kayak on the Russian River. The town is also home to SingleThread, a Michelin starred farm restaurant and inn.
September and October are harvest season, which is beautiful but busy on weekends. Book a table and a room early.
25. Port Townsend, Washington
Port Townsend is a Victorian seaport on the tip of the Olympic Peninsula, about two hours from Seattle with a ferry ride across Puget Sound. Its downtown along Water Street and up on the bluff is a National Historic Landmark district.
Fort Worden State Park is a coastal fort from 1902, where An Officer and a Gentleman was filmed. Walk out to Point Wilson Lighthouse at the edge of the park for views across the water.
June through September is the best time to go, and the Wooden Boat Festival fills the harbor in early September.
More Weekend Getaway Ideas
A few more places almost made the list. Hood River, Oregon is about an hour from Portland in the Columbia River Gorge, with windsurfing on the river and farm stands along the Fruit Loop.
Stowe, Vermont sits at the foot of Mt. Mansfield, the highest peak in the state. Lake Geneva, Wisconsin has a public shore path of about 21 miles past grand old lake mansions, only an hour and a half from Chicago.
Mendocino, California is a clifftop village three and a half hours north of San Francisco. Bar Harbor, Maine is the gateway to Acadia National Park, and Saratoga Springs, New York has mineral springs and a summer horse racing season. Any of them would make a great weekend getaway too.
How To Plan A Weekend Getaway
The best weekend getaway ideas are the ones you can actually reach. Aim for about three hours of driving or a short direct flight, so the trip doesn’t eat half of Saturday.
If you can, leave Friday afternoon or take the day off. Two full days in a small town feels completely different from one and a half.
Small inns and bed and breakfasts fill up fast in peak seasons, especially fall foliage weekends and summer on the water, so book early. Spring and late fall are often quieter, and some places, like Mackinac Island and mountain roads in Colorado, have seasons worth checking before you go.
Final Thoughts
The best part of a weekend getaway is how little it asks of you. A couple of nights, a walkable main street and one great meal can feel like a real vacation.
Pick the one closest to home, or the one you’ve been meaning to see for years, and put it on the calendar. Most of these weekend getaway ideas are even better the second time.
