25 Best Small Town USA Weekend Getaways

By VI Staff on January 2, 2021 - Updated

Best Small Town Weekend Getaways for Couples

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When you feel the need to escape the nine-to-five routine and let your hair down somewhere new and exciting, try imagining yourself in one of these wonderful weekend getaway destinations. Since there is no such thing as the perfect one-size-fits-all destination, our list of 25 enticing weekend escapes has something for everyone. Whether you love long romantic walks on the beach or prefer hiking in the mountains, we have just the place lined up. CDC information for travelers. Hours/availability may have changed.

1.Woodstock, VT

Woodstock, VT is an ideal getaway destination for active couples, offering a wide variety of outdoor activities all year round. The town is located in the Green Mountains of Windsor County and is easily accessible for a quick weekend break. If you visit in winter, you can spend your days enjoying cross-country and downhill skiing and then curl up besides a romantic log fire. In spring and summer, you can go hiking, biking, fishing, or rock climbing followed by a romantic dinner in a top restaurant. Autumn is a great time to take a scenic drive along the Vermont Scenic Byway to see the fall colors at their best or take to the air on a romantic hot-air balloon excursion. More Places to Visit in Vermont

2.Seabrook Island, SC

Seabrook Island is located just 30 miles south of the historic city of Charleston in South Carolina and offers visitors an idyllic beach-side destination with great facilities and plenty of activities. The island is a private gated community that boasts over three miles of pristine white-sand beaches and a large variety of accommodation options. The best way for you to explore the island is on two wheels along many miles of scenic routes – bike rentals are available at Alligator Bike or the Island Bike and Surf Shop. Anticipate romantic sunset beach walks (or beach horse-back riding), island-hopping boat charters, golf, tennis, and swimming. There are two large swimming pools, a fitness center, and great shopping and dining at Freshfields Village.

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3.McMinnville, OR

McMinnville is located in the heart of the famous Willamette Valley, Oregon’s premier wine producing region, which is home to over 700 vineyards and more than 500 wineries. In addition to being a Mecca for food and wine connoisseurs, the town has a host of other interesting attractions including the Evergreen Aviation Museum, the Yamhill Valley Heritage Center, and a thriving arts and culture scene. A McMinnville Wine Passport is your ticket to an entertaining and educating history/wine-tasting walk through the impressive historic district where you will find an amazing variety of local wines available for tasting or purchase. Accommodation options range from smart rental apartments to romantic B&B’s and hotels, many of which are housed in charming Victorian buildings. Places to Visit in Oregon

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4.Doylestown, PA

Doylestown, PA is an interesting and unusual getaway destination located just 27 miles from Philadelphia and about 80 miles from New York City, offering a good mix of indoor and outdoor weekend activities. The remarkable Fonthill Castle and Museum is the town’s most popular attraction and a must-see for all visitors. Other interesting historic attractions include the 1927 Tudor-style Aldie Mansion, the Pearl S. Buck House, the Mercer Museum, and the Moravian Pottery and Tile Works. Art lovers should not miss the Pennsylvania Impressionist Collection at the James A. Michener Art Museum. Foodie couples can visit the Doylestown Farmer’s Market, sample a brew at the Doylestown Brewery, do some wine tastings, or sign up for a Bucks County Food Tour. Besides history and food, the town offers several options for outdoor fun including hiking, biking, and rock climbing. More Places to Visit in PA

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5.Lookout Mountain, AL

At Lookout Mountain in north-eastern Alabama, you and your partner can escape the hustle and bustle of the city and spend a romantic weekend getting back to nature in one of the state’s most scenic areas. You can rent a romantic log cabin in the DeSoto State Park where you can go hiking and biking and enjoy a picnic surrounded by natural beauty. Other outdoor activities include horseback riding, fly fishing in the Little River, rock climbing, rappelling, and kayaking. The Sequoyah Caverns beckon visitors to come and discover the beautiful underground “Looking Glass Lakes,” and in winter you can partake in all the snow sports at the Cloudmont Ski Resort. More Things to Do in Alabama

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6.San Luis Obispo

Could San Luis Obispo be California’s best kept secret? Whether you are looking for a fabulous foodie destination offering genuine farm-to-fork cuisine and spectacular local wines or want to enjoy long romantic beach walks, you will find both in abundance in San Luis Obispo. The city boasts over 300 days of sunshine a year, which means that you can enjoy wonderful outdoor activities all year round – take your pick from hiking, biking, surfing, zip-lining, and even dune riding. If your idea of a perfect couple’s weekend includes a little culture, you can visit the Performing Arts Center, catch a show at the Great American Melodrama, or visit the San Luis Obispo Museum of Art and round off your day with an open-air concert at the amphitheater at Paso Robles.

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7.Annapolis, MD

Historic cobbled streets dating back to the 17th century and over 300 glorious floral hanging baskets contribute to the romantic atmosphere of Annapolis, one of Maryland’s most popular couple’s retreats. For a memorable day out, you can take a Chesapeake Bay cruise on the 74-ft Schooner Woodwind (if you are feeling particularly romantic you can book an overnight breakfast package) to see the beautiful coastline from the bay. Back on land, you can tour a couple of well-preserved historic homes and gardens, including the William Packer House (and two-acre tiered garden) and the Charles Carroll House and Gardens. There are plenty of accommodation options ranging from quaint to opulent – take your pick and settle in for relaxing coastal weekend break. Things to Do in Annapolis

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8.Aspen, CO

Nestled in the heart of the Colorado Rocky Mountains, Aspen, CO is best known as a premier winter sport destination. What many people do not know is that Aspen is an ideal year-round couple’s getaway destination offering some really special romantic activities that perfectly set the scene for a proposal or a special anniversary. You can go hot air ballooning or paragliding over the stunning mountain scenery (usually followed by a champagne breakfast), or opt for the equally spectacular (but less expensive) option of riding the gondola to the top of Aspen Mountain to enjoy a romantic moonlit Friday-night dinner. In summer, you can add kayaking and white-water rafting to the list of activities. Wind down your day with a couple’s massage at the spa or encourage togetherness by taking a couple’s cooking lesson.

9.Bar Harbor, ME

Bar Harbor is located off the coast of Maine and has been a favorite holiday destination since the early 19th century. The island offers couples a unique environment for romantic relaxation and outdoor recreation. The most popular activities for active visitors include walking, hiking, and cycling along the many trails that offer wonderful coastal scenery and the chance to glimpse some of the extravagant holiday mansions. Romantic excursions include whale watching tours, lobster fishing excursions, guided kayaking, and photographic and rock-climbing tours. For a change of pace, you can visit a couple of museums, galleries, and shops and round off your day with a sublime Maine lobster dinner. Things to Do in Bar Harbor

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10.Beaufort, NC

The North Carolina town of Beaufort was established back in 1713 and has over 300 years of history and charm to showcase to visitors. The town has won several awards, including “Best Small Town” and “Most Romantic Small Town” and deserves a place on every couple’s must-see list. You can join a guided tour (on foot or bicycle) to explore the town’s legendary maritime history and learn all about the legends of Blackbeard, whose pirate ship went down in the estuary (recovery work is under progress). There are dozens of historic homes to see, and the revitalized waterfront is the ideal place to sip a coffee or a cocktail. You can go wreck diving along the coast or opt for some dolphin watching or sunset cruising with Lookout Cruises.

11.Burlington, VT

Burlington, Vermont is an ideal couple’s weekend getaway destination offering a wide variety of fun outdoor and indoor attractions. Fall is without a doubt the most romantic time to visit the city when the autumn colors are just about blinding and the weather is perfect for hiking, biking, and other outdoor activities. Why not join a Segway tour or hop aboard the Historic Burlington Trolley to get your bearings? If you happen to experience less than perfect weather, you can still have fun exploring the ECHO Aquarium and Science Center and the Fleming Museum of Art. Add a touch of sophistication to your romantic weekend by attending the Vermont Symphony Orchestra or watching the Vermont Stage Company in action before lingering over a romantic fireside dinner. Things to Do in Burlington

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12.Carmel-by-the-Sea, CA

Carmel-by-the-Sea is one of the most popular getaway destinations in California. The quaint small town is nestled among verdant greenery above a stunning white sand beach, which is perfect for long, romantic sunset walks. The town is filled with charming alleys and passageways leading to unique shops, boutiques, and restaurants, and there is a great selection of outdoor activities for energetic couples, including kayaking, surfing, paddle-boarding, and snorkeling. You can go hiking in the Point Lobos State Reserve, catch a concert at the Sunset Cultural Center, or join a guided 90-min Carmel Art Tour. Foodies can have fun exploring the burgeoning food scene in the village and visiting 15 tasting rooms to sample local wines. Things to Do in Carmel

13.Charlottesville, VA

A great combination of charming historic buildings, great shopping and dining, wide open outdoor spaces, and an emphasis on the arts make Charlottesville a wonderful choice for a romantic couple’s getaway weekend. You can take a walking tour to uncover the town’s many historic buildings, including Monticello, the former home of Thomas Jefferson, which is a UNESCO World Heritage Site. If you love the arts, you can visit the Fralin Museum of Art and the Les Yeux du Monde Art Gallery before heading to one of several renowned live music venues. There is plenty of outdoor fun to be had, including hiking, biking, and kayaking, or you can head out of town for some fruit picking or to follow the famous Monticello Wine Trail or the Brew Ridge Brewery Trail. More Charlottesville Tourism

14.Door County, WI

If you are yearning to find the ideal place to escape the city and enjoy all the pleasures that come with 300 miles of Lake Michigan shoreline, Door County in Wisconsin is waiting to welcome you. An abundance of beaches, bays, coves, and inlets offer endless opportunities for romantic beach walks and tide pooling, and if you are into boating and water sports there are 12 marinas and three inland lakes to enjoy. Adventurous couples can try fishing, kite surfing, scuba diving, and much more. If you prefer to keep your feet dry, you can spend your weekend exploring the scenic peninsula on foot or by bike or take a Segway or helicopter tour. You can also make your way around the eleven historic lighthouses and visit some local art galleries or studios.

15.Friday Harbor, WA

When it comes to choosing a great romantic getaway destination in Washington State, you will find Friday Harbor on San Juan Island hard to beat. You can start your visit by taking a romantic walk or cycle along the beach or get more active and hire a stand-up paddleboard from Springtide Paddlesports. When you are not hiking or walking, you can spend some time relaxing on the beach, exploring the island on a moped from Suzie’s Mopeds, or tantalizing your taste buds at one of the many inviting restaurants and coffee shops. On the odd rainy day, you can visit the Whale Museum, take a Jolly Trolley Tour, or stroll through the many local art galleries and shops.

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16.Galena, IL

Galena, Illinois is a charming historic small town that genuinely offers something for every visitor regardless of you taste in leisure activities. The town is renowned for its great collection of well-preserved historic buildings, and if you love learning about history you can spend hours exploring the huge historic district on foot. If you prefer nature to history, you can go hiking and cycling in the Casper Bluff Land and Water Reserve or go for a romantic stroll through the West Street Sculpture Park or the beautifully themed Linmar Gardens. Art lovers should not miss the Galena Center for the Arts, while foodies can explore diverse taste sensations at a wine and food pairing at the Galena Cellars Winery and Vineyard.

17.Ithaca, NY

Nestled on the shores of Cayuga Lake (the largest of the Finger Lakes) and surrounded by more than its fair share of natural beauty, Ithaca is an ideal place to escape to for a couple’s weekend getaway. You can spend your days enjoying the abundance of waterfalls and gorges (over 100 waterfalls wait to be uncovered) on one of the many hiking, walking, and biking trails that meander through the picturesque area, or you can head for the lake to enjoy a wide variety of water sports and boating opportunities. The campus of Cornell University is home to some great museums and galleries to keep you occupied on rainy days. There are many great options for accommodation, ranging from cozy lake-side log cabins to charming country-style inns and hotels.

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18.Montauk, NY

Montauk occupies an idyllic location at the eastern-most tip of Long Island, New York, and is almost completely surrounded by the Atlantic Ocean, offering many miles of beaches, scenic hiking, and cycling paths. City dwellers can look forward to enjoying wide open spaces made just for relaxation. There are a number of state parks where you can go hiking, biking, fishing, wildlife viewing, sailing, boating, and chartered fishing expeditions are all part of the fun. During the summer you can catch a ferry to colorful Martha’s Vineyard or grab a seat at Gosman’s Dock to watch the world go by as you feast on fresh seafood or listen to a summer concert, while in winter you can enjoy cross-country skiing and inviting log fires.

19.Portsmouth, NH

You will need more than a few days to fully do justice to the many and varied attractions on offer in Portsmouth, New Hampshire. Portsmouth dates back to 1623 and is home to a wealth of interesting museums and historic sites, but it is the town’s marvelous Seacoast location that attracts large numbers of visitors each year. A few of the many activities on offer include relaxing or walking on Hampton Beach, going on a whale-watching boat tour, or setting off on a Lobster Adventure Tour. You can combine history and wonderful scenery on the Lighthouse trail or have hours of fun at New England’s largest water park. Foodies will enjoy visiting a few local breweries and lingering over a feast of fresh seafood at one of many excellent restaurants.

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20.Sag Harbor, NY

Historic Sag Harbor has long been a popular weekend retreat for New Yorkers wanting to relax and feel the sea breezes in their hair. Sag Harbor was settled around 1700, and today the town is home to an extensive collection of beautifully preserved historic buildings that now house a variety of interesting small-town shops and galleries. There are a couple of interesting museums to visit on rainy days, including the Sag Harbor Whaling and Historic Museum and the Custom House Museum. The pull of the ocean is evident everywhere you go in Sag Harbor so it is hardly surprising that sailing, fishing charters, and scenic cruises are highly popular. Other popular activities include golfing, boating, kayaking, and wildlife watching.

21.Sanibel, FL

Sanibel Island is a wonderful vacation destination located on a barrier island off the west coast of Florida. Sanibel is almost completely surrounded by water (there are over 15 miles of beaches) and offers visitors an almost endless menu of outdoor activities all year round. The long pristine beaches are perfect for romantic sunset walks, and during the day you can simply relax under a gently swaying palm tree or get up and be active as you try surfing, wind-surfing, kayaking, snorkeling, or scuba diving. Other island activities include bird watching, nature and historic tours, hiking, biking, golfing, and visiting various wildlife and science centers. Foodies will enjoy sampling innovative cuisine at some of the 50 restaurants and cafes.

22.Sonoma County, CA

The spectacular coastline, vineyards, wineries, forests, and cities of Sonoma County have been a popular getaway destination for generations of visitors and offer the ideal backdrop for a romantic couple’s weekend. Imagine vineyards that stretch as far as the eye can see, dotted with fairytale Chateau’s like Ledson Winery or Chateau St. Jean. You can take a guided tour or explore at your own pace. There are wonderfully romantic accommodation options all over Sonoma County that make the perfect destination for a honeymoon or special anniversary. Outdoor enthusiasts can go hiking, biking, kayaking, and boarding or hop aboard a whale-watching charter. Charming towns and villages will entice you to explore a feast of visual and performing arts and a myriad of great restaurants invite you to sip wonderful local wines and taste the and farm-to-fork cuisine.

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23.St. Simon’s Island, GA

St. Simon’s Island on the coast of southern Georgia has won multiple awards for being one of America’s most romantic/favorite beach towns, and it ticks all the boxes for a memorable couple’s getaway. You can spend your days relaxing on the beach or opt for some exercise and rent a bike to explore 20 miles of cycling trails. Water sports are extremely popular, and you can try canoeing, kayaking, sailing, boating, and island-hopping (there are several marinas offering charters and rentals). If you prefer exploring the arts, you will find plenty of galleries, concert venues, and theaters offering a full seasonal menu of shows. Other attractions include nature tours, 63 holes of golf, and the Summer Waves Water Park.

24.Traverse City, MI

Nestled along the shores of Lake Michigan, Traverse City is an ideal getaway destination with a wide range of interesting activities to fill your weekend. Before you set off to try out some outdoor activities, you may like to check out the town’s thriving arts scene at the Interlochen Center for the Arts or listen to the Traverse Symphony Orchestra perform at the City Opera House. Outdoor activities include hiking the famous Sleeping Bear Dunes, biking, fishing, and a host of winter sports such as cross-country skiing, snowboarding, and snowshoeing. The region is famous for its wineries and micro breweries, and there are several tours you can join to sample some of the best brews and wines.

25.Winter Park, FL

Winter Park is located in Orange County, central Florida. As the name indicates, the city was once almost purely a winter bolt hole for people wanting to escape the harsh northern winters, but today visitors come all year round to enjoy the thriving arts and culture scene and the abundance of outdoor activities. Weekenders can attend one of the regular festivals and events that take place in the city’s seventy parks, visit some interesting museums and art galleries, enjoy live theatre and concerts, or tour the Hannibal Square Historic Neighborhood. Outdoor activities include canoeing and kayaking, hiking, cycling, fishing, golfing, and boating. In addition to all these activities you can find an endless list of attractions in near-by Orlando.