Best Weekend Trips on the East Coast This Fall

Located in southwestern Connecticut, Fairfield County is a great antiquing destination. But one cannot live by retail alone: Here are a couple of eating and drinking options:

Oktoberfest is such a big deal in Connecticut that the festivities start in September and continue deep into the next month. Food, music, and beer are offered at multiple festivals; some events promise celebrity chefs, Bavarian dancers, ski-lift rides, games and curated pairings of food and brews.

On October 6, more than 30 chefs will gather in Westport for the annual New England ChowdaFest; visitors get to sample multiple varieties of chowder and vote for their favorites. The event raises funds for Food Rescue U.S., a charity that redistributes unused food from restaurants to shelters.

A tradition of 30 years, the 2019 Sea Witch Halloween and Fiddlers’ festival is scheduled for October 25-27 in Rehoboth Beach and Dewey Beach, Delaware. Costumed marchers, elaborate floats, and string bands parade through town; there’s even a separate parade for decked-out dogs! Games, trick-or-treating, hayrides and pony rides are among the activities. There’s also a 5K race, a broom-tossing contest, an abundance of live music, a horseshow and history hikes on the agenda, among a plethora of other things to do.

Destin, in Florida’s panhandle, hosts a litany of special events in the fall season. Try feasting on foods prepared in at the Eggs on the Beach cook-off, scheduled for September 28. The Destin Seafood Festival, a local mainstay for more than four decades, is expected to draw crowds October 4-6, for a weekend of music, art, and of course, noshing on tasty delights from the sea. Or you can reel the fish in yourself at Destin’s annual Fishing Rodeo, which runs throughout the whole month of October. Another option: Relaxing with a couple of brews at the Baytowne Wharf Beer Festival, October 11-12, and enjoying the local sights—including migrating Monarch butterflies and stunning sunsets.

It’s raining beach balls in Panama City Beach, Florida, this fall! About 8,000 of the brightly colored inflatables will fall from the heavens at the Pirates of the High Seas Fest, October 11-13. Music, fireworks, magic shows, parades and storytelling are also on the schedule at this free annual event.

The fun continues October 14-20, at Schooners Lobster Festival and Tournament, with music, a beach party, sand-sculpting contests and chowing down on succulent shellfish among the activities.

Revelers at the Tybee Island Pirate Fest, October 10-13, are invited to dress like a pirate and join in the fun at the Buccaneer Ball. There’s something for everyone, whether you like petting zoos and bounce houses or grog and boogying.

The Savannah Jazz Festival (September 22-28) presents a mix of local and regional favorites with nationally and internationally hailed players like Vanessa Rubin and Anat Cohen.

Oktoberfest on the River (October 4-6) includes dancing, Weiner Dog Racing and other fun events, along with plenty of food and drink vendors. Head for the Shalom Y’all Jewish Food Festival (October 27) for your fill of deli sandwiches, latkes, blintzes, challah and other savory and sweet delights, along with dancing, music and entertainment.

There’s plenty to do year-round in Acadia National Park, as more than 3.5 million annual visitors can attest. Though it’s among the top 10 most-visited national parks, the crowds thin out as autumn arrives. The varied terrain includes rugged shorelines, plus lakes and forest trails. Check out the splendor of the fall foliage on the 158 miles of hiking trails. Camping is permitted through November 10.

Waterfalls, lakes, wildlife, dramatic gorges and rugged mountains await you in western Maine’s Grafton Notch State Park. A popular hunting and fishing destination, the park is also a great spot for picnicking, enjoying the fall colors, birdwatching, and camping. Try exploring on foot along trails running the gamut from casual strolls to some of the most challenging sections of the Appalachian Trail.

There’s lots of fun and adventure to be had on the water near Kennebunkport, Maine, on vessels large and small. Take a sail on a traditional two-masted schooner on which passengers can kick back, relax and enjoy the views, or try their hand at working the sails. Kayaking, fishing charters, whale watching and eco-tours are also on offer, as are voyages on lobster boats and ferries.

It’s safe to guarantee that visitors to Maryland’s Eastern Shore are in no danger of going hungry this fall. Crab picking and oyster shucking are on the agenda October 19 at Tilghman Island Day; on November 2, the island hosts the Oyster Jam & Brew Fest, with more than a dozen beers. St. Mary’s County is the site of U.S. Oyster Festival October 19-20.

When it comes to relaxing with a drink, St. Michaels, Maryland, offers an interesting range of venues—and libations. Wine aficionados can learn about a variety of whites and reds on a two-hour wine-tasting sail, or some may prefer the sunset cruise supplemented with Champagne and snacks. Complimentary rum tasting and distiller-led tours are on the Saturday schedule at Lyon Distilling, which produces close to a dozen varieties of the potent potion. The beer-tasting room at Eastern Shore Brewing opens at noon daily; in the past decade, the brewery has won multiple awards for its seasonal and year-round varieties. Behind-the-scenes brewery tours are offered by appointment.

The changing leaves in the Berkshires are attraction enough, but there’s more to the region than that. The FreshGrass Festival takes place at the Massachusetts Museum of Contemporary Art September 20-22, featuring performers including the Kronos Quartet, Mavis Staples, and Alison Brown. Take in Mass MoCA’s stunning contemporary art exhibitions while you’re at it.

Other fun regional events include Williamstown’s Wind-Up film festival (October 15-18) and fall theater productions at Shakespeare & Co. in Lenox.

It’s not exactly beach season, but you can still connect with the water at Duxbury Bay Maritime School, which offers educational and recreational programs for all ages, including maritime science and dockside yoga. A climb to the top of the Myles Standish Monument will reveal Duxbury’s scenic vistas, likely featuring some grand fall foliage. Learn about the town’s history as a shipbuilding center at the Duxbury Rural & Historical Society, which also offers tours of historical houses into November. Colonial-history buffs can visit Plymouth Rock, in nearby Plymouth.

A New Hampshire fall weekend around Lake Winnipesaukee can be bucolic, adrenaline pumping or both. Consider mountaintop yoga or moonlight zip-lining, both offered at Gunstock Mountain Resort. You can take a tai chi course or a spirit encounter tour at nearby Canterbury Shaker Village this fall. Other local activities include hiking, boat rides, museum visits and rope courses, as well as antiquing, leaf peeping and more.

The Laconia, New Hampshire, Pumpkin Festival is no homespun, small-town shindig. Scheduled for October 18-19 this year, past events have attracted more than 40,000 annual visitors. Yes, there will be pumpkin carving and crafts vendors, but also pumpkin bowling and a 34-foot-high jack-o’-lantern tower. Bungee jumping, a zombie walk, car show, beer garden, live music, amusement rides and more are in the 2019 lineup.

Cape May, New Jersey, is known for its beaches and oceanfront Victorian mansions, but who knew it’s also a paranormal hot spot? There are a couple of ways to dig deeper into the topic this month: the Ghosts of Cape May Trolley Tour and the Historic Haunts Combination Tour or meet up with medium Craig McManus at a number of historic locations or for a Ghost Walk.

In between spooky tours, check out the special events at nearby wineries, local theater productions, and enjoy Oktoberfest (September 28).

Lots of towns have half marathons, but how many of them take place on former Olympic facilities? The route of the Lake Placid Half Marathon (October 12) includes some of the sites of the 1980 Winter Olympics. If you’re not into running, you can visit the site for a high-level view of all the colors of autumn from the top of the 120-meter ski jump.

Besides being a leaf-peepers delight, the Adirondack region hosts a pair of Oktoberfests: one at White Face Mountain (September 28-29) and another at Lake Placid Pub and Brewery (October 5). Movie buffs may want to check out the Lake Placid Film Festival (October 23-27). The Flaming Leaves Golf Tournament is scheduled for September 21-22.

Lots of regions hold pumpkin festivals at this time of year, but New York’s Catskills region goes a different way with an annual Cauliflower Festival. Now in its 16th year, the September 21 event in Margaretville offers traditional music, quilting demonstrations, a tractor parade, pony rides, a petting zoo, artists and crafts vendors, and of course, cauliflower.

Other Catskills fall fun includes a murder mystery train ride (October 13); Taste of the Catskills Festival with food, wine, and beer. Or simply savor the scenic fall views while strolling the Walkway Over the Hudson.

It’s off-season in the Outer Banks, crowds have thinned out, but there’s still lots going on every weekend. Celebrate the marine culture of the Outer Banks this fall at Manteo’s Surfalorus Film Festival (September 19-21), presenting a mix of surfer flicks and documentaries focusing on all things aquatic.

Later in the fall, Festival Latino de Ocracoke (November 8-10) promises events the whole family can enjoy, including food, music, arts and crafts and more.

Fall colors transform the Blue Ridge Mountains, and for more than a half century, Mount Airy has celebrated the change of season with its Autumn Leaves Festival (October 11-13). Upwards of 200 craftspeople are expected to be on hand, demonstrating their techniques and offering their wares. Regional culinary specialties described as “food for the soul,” will pique appetites, including ham, biscuits, collards, barbecue and Amish doughnuts. Live old-time music, bluegrass and gospel will provide a suitable soundtrack for a weekend of outdoor fun.

Fall for Greenville (October 11-13) bills itself as “the Southeast’s most popular outdoor festival.” Music lovers will have an array of genres to choose from among the 60+ musical acts scheduled. There are tributes to Aretha Franklin, Tom Petty and Jaco Pastorious, and performers covering genres like Texas swing, indie folk, neo jam grass, rockabilly, alt country, and honky-tonk. It’s easy to work up an appetite while grooving to the sounds, and more than 45 restaurants are committed to showing off their best culinary moves to take care of that need.

Nothing says fall like changing foliage, corn mazes, harvest time, pumpkins, and, if you’re in Newport, seafood. All things autumnal will be celebrated in this charming coastal town in the coming months, with a wealth of events scheduled.

Among the most unusual is the Astronomy Bonfire held at the Blithewold Mansion (October 28). It’s a unique chance to enjoy a star show and discussion about the constellations, before warding off the evening’s chill by sipping hot cider around an open fire.

Hop on the ferry to Block Island for a relaxing weekend getaway. Once the beach crowds have departed, the pace slows and there’s an opportunity to discover the beauty of the island at your leisure. Visitors can stick with the water on a fishing charter or spend time on shore, where there’s a wealth of exploring to be done. Recommended sites include nature and wildlife preserves, beaches and lighthouses, and even the Sacred Labyrinth. So take a hike, rent a bike or ride a horse and get in touch with the great outdoors.

Why should zombies, witches and pirates get all the attention? If you’re ready for something new this Halloween season, consider the South Carolina Bigfoot Festival scheduled for October 25-26. Activities include a 5K Squatch (as in Sasquatch) Stroll, a blood drive, live music, food, a parade, speakers, and a research outing to cryptid activity hot spots.

Situated in the Appalachian foothills, Westminster boasts more than two dozen waterfalls in the area, as well as fishing, whitewater rafting, horseback riding, golf and hiking, which could add up to a fun fall family weekend.

Hilton Head Island’s fall outdoor concert series are in full swing, as evidenced by Music & Taste on the Harbour, featuring dancing to live bands every Thursday through October 17.

Car buffs will be in their element around classic rides displayed at the Carolina Dreamers Car Club’s Cruise-in (October 24), Concours d’Elegance & Motoring Festival (October 24-November 3), and the Carolina Dreamers Car Club’s Trunk-o-Ween Cruise-In (October 31).

Those who like to focus on food—and who doesn’t—can chow down at the Hilton Head Island Shrimp Festival (September 20-21), the Gullah Food Festival (October 19), or the Italian Heritage Festival (October 26).

Enjoy the Shenandoah National Park’s waterfalls, woods and vistas from the Skyline Drive, and get a glimpse of the cosmos miles from light pollution at Night Skies stargazing in Shenandoah (October 4).

Another way to see the region is by mapping out a festival itinerary. Among the events to consider are the 44th Mountain Heritage Arts and Crafts Festival (September 27-29), the 50th annual Page County Heritage Festival (October 12-13), the Shenandoah Fall Foliage Bike Festival (October 18-20) and the Grilled Cheese and Tomato Soup Festival (November 2).

Fans of beer and bluegrass music will find much to love about the Strings & Things festival (September 26-29). In addition to concerts at the Salem Civic Center and the Salem Farmers’ Market, there will be free performances at two of the town’s craft breweries.

In nearby Floyd, Virginia, the Floyd Country Store is a long-time gathering place for musicians sharing regional traditions, musical styles and stories. There are free jam sessions featuring bluegrass and old-time music each Sunday. Friday nights at the Floyd Country Store kick off with gospel music followed by two dance bands that are practically guaranteed to get everyone out of their chairs and onto the dance floor.

The fall foliage is a powerful draw to the Blue Ridge Mountain Parkway, with its scenic vistas including the iconic Marby Mill waterwheel, covered bridges and other reminders of times past.

Beyond leaf-peeping, there’s a lot to see and do in nearby towns. Take a gander at some classic cars and maybe pick up a vintage item you’ve always craved at the Maggie Valley Swap Meet (September 26-28). For wheels of another kind, the Peanuts Great Pumpkin Patch Express delivers a vintage train ride through the mountains on October weekends, themed after the classic Halloween story, “It’s The Great Pumpkin, Charlie Brown.”