When the air turns crisp and the leaves blaze in shades of red, orange, and gold, the Eastern U.S. transforms into a fall-lover’s dream. And for families with younger children, there are plenty of towns that go all-out for autumn — from pumpkin patches and apple cider to family-friendly Halloween fun (without too many jump-scares).

I’ve rounded up one or two destinations in each Eastern state where you can spend a long weekend enjoying the season to its fullest. Whether you want scenic foliage, spooky (but kid-appropriate) festivities, or just a cozy fall getaway, these towns have something magical to offer.

Don’t want to read everything? Click what state you’re interested in viewing your best fall options below:

Ready to make your fall family weekend a reality? Contact me today! We can talk locations, hotel options, and additional things to do to make one easy fall vacation package!

Maine

Bar Harbor – Bar Harbor is your gateway to Acadia National Park’s stunning fall foliage—think Cadillac Mountain sunsets, scenic carriage roads, and easy nature walks perfect for little legs. Mid-October typically brings peak leaf colors, and you can map your visit around the leaf peeping tours spotlighting Cadillac Mountain, Jordan Pond, and coastal drives. Hotels range from $250-$500/night on average for the fall and there are many options for guided or self-guided tours of Acadia, Bar Harbor ghost tours, and boat rides!

Kennebunkport – This quaint coastal town vibrates with autumn charm—think pumpkin patches, hayrides, cozy cider tastings, and boutique resort events. Families can enjoy ghost tours, sailing trips and more throughout October. It’s relaxed, cozy, and perfect for multi-generational escapes. Hotels range from $150-$400/night on average for the fall.

New Hampshire

North Conway – Nestled in the White Mountains, North Conway has family-friendly scenic train rides, apple orchards, and pumpkin festivals. It’s a leafy haven unfolding against a backdrop of scenic trails and small-town charm. The Return of the Pumpkin People invites families to tour delightful pumpkin-headed displays through town this fall season. Hotels range from $125-$250/night on average in the fall.

Portsmouth – Portsmouth, NH is a gem for families looking to soak up the magic of fall. This charming seaport town comes alive with autumn color, offering something for everyone— from the Fall Family Fun Fest to the city’s festive Halloween parade and community trick-or-treating. Add in crisp afternoons spent wandering Prescott Park, playful adventures on Peirce Island, and a cozy stroll through downtown with its boutiques and cafés, and you’ve got the perfect mix of history, outdoor fun, and seasonal celebration. Portsmouth delivers fall charm in every direction, making it an easy choice for a family weekend escape. Hotels range from $200-$400/night on average in the fall.

Vermont

Stowe – Stowe is a postcard-perfect spot to experience Vermont’s famous fall foliage with kids. Families can take a scenic gondola ride up Mount Mansfield to admire the brilliant colors from above or explore easy trails like the Stowe Recreation Path for a stroller-friendly way to soak in the scenery. The town’s harvest festivals bring hayrides, pumpkin patches, and live music, while cider mills and creameries offer sweet treats the whole family can enjoy. With its blend of outdoor adventure, cozy local shops, and plenty of room to run and play, Stowe makes fall feel magical for families with little ones. Hotels range from $250-$600/night on average in the fall.

Woodstock – Woodstock captures the quintessential New England autumn—charming village greens, historic covered bridges, and family-friendly farms bursting with fall activities. Families can wander through apple orchards, take in colorful foliage drives along quiet country roads, or stroll the walkable downtown filled with bookstores, cafés, and sweet shops. Whether you’re snapping photos on the Ottauquechee River bridge or cozying up with hot cocoa after a day outdoors, Woodstock offers a relaxed, picture-perfect fall escape that little travelers will love. Woodstock is home to mostly rental homes, which average $250-$600/night in the fall.

Massachusetts 

Salem – Famous for its witchy history, Salem is one of New England’s most spirited destinations in October, and it offers plenty for families with younger children too. During the month-long Haunted Happenings Festival (October 1–31, 2025), kids can enjoy costume parades, pumpkin decorating, and family-friendly ghost tours. Add in harbor cruises with stunning fall foliage views and Salem becomes much more than spooky—it’s a festive, cultural, and colorful fall escape the whole family can enjoy. Hotels range from $300-$600/night on average in the fall.

Stockbridge – Nestled in the Berkshires, Stockbridge is the definition of a storybook New England town in the fall. Families can take easy nature walks at nearby Naumkeag, where gardens transform with autumn colors and seasonal displays or learn more in the Norman Rockwell Museum. Local farms offer apple picking, hayrides, and cider donuts—perfect for a crisp afternoon outing. The charming Main Street, famously painted by Rockwell himself, is ideal for strolling with little ones, while nearby Berkshire attractions like hiking trails and pumpkin festivals round out the experience. Stockbridge’s slower pace and small-town warmth make it a cozy, family-friendly place to savor autumn together. Stockbridge is mostly rental homes, which average $250-$500 in the fall.

Connecticut

Mystic – Mystic blends seaport charm with cozy fall fun, perfect for younger kids. In October, fall festivals bring live music, hayrides, and plenty of cider treats, while nearby orchards and pumpkin patches invite families to pick their own seasonal goodies. Add in a stroll through downtown Mystic—with its toy shops, ice cream parlors, and views of the historic drawbridge—and you’ve got an easy, family-friendly destination that feels like a classic New England fall postcard. Hotels range from $200-$300/night on average in the fall.

Litchfield – Litchfield is the heart of Connecticut’s countryside charm, and fall makes it especially magical for families. Bright foliage blankets the rolling hills, and local farms invite little ones to pick pumpkins, sip fresh cider, and wander through corn mazes. At White Memorial Conservation Center, families can enjoy easy trails, boardwalk strolls, and wildlife spotting—perfect for young explorers. The historic town green and surrounding shops offer a relaxed afternoon of browsing books, toys, and treats, while nearby apple orchards make for the quintessential autumn outing. Litchfield delivers a slower-paced, picture-perfect fall escape for families with younger children. Litchfield is mostly rental homes, which average $300-$500/night in the fall.

Rhode Island

Newport – Newport may be famous for its summer mansions and coastal charm, but fall makes this seaside city extra inviting for families. The crisp air is perfect for strolling the Cliff Walk, where little ones can take in ocean views framed by autumn colors. Families can explore the grand mansions with seasonal tours—many offering harvest or Halloween themes in October—or hop on a harbor cruise to admire both foliage and historic lighthouses. Local farms just outside town provide pumpkin patches, hayrides, and cider treats, while downtown Newport bustles with cozy cafés, toy shops, and fall festivals. With its mix of seaside beauty, cultural landmarks, and festive fun, Newport is an easygoing, picture-perfect choice for a family fall getaway. Hotels range from $250-$500/night on average in the fall.

New York

Sleepy Hollow – Sleepy Hollow is one of the most iconic Halloween destinations in the country, and it delivers plenty of family fun. The town leans into its legendary tale with kid-friendly storytelling events, costumed parades, and lantern-lit evening walks. The Great Jack O’Lantern Blaze (late Sept–Nov 2025) amazes kids with thousands of glowing pumpkins carved into incredible displays. For little ones, daytime visits to pumpkin patches and scenic Hudson Valley hikes provide a balance of fresh air and festive fun, making Sleepy Hollow a must-see for families craving a storybook Halloween experience. Hotels range from $250-$400/night on average in the fall.

Lake Placid – Tucked in the Adirondacks, Lake Placid is a gorgeous fall getaway where families can mix outdoor adventure with seasonal fun. The village comes alive in autumn with brilliant foliage, best seen on a scenic drive along the Adirondack Loj Road or by taking a gentle hike on kid-friendly trails like Cobble Hill. Families can ride the gondola at Whiteface Mountain for sweeping views, explore Mirror Lake with a leisurely stroll or paddle, and visit the Olympic sites that spark kids’ imaginations. Local farms and cider mills add festive flavor with apple picking and donuts, while downtown Lake Placid offers toy shops, cafés, and cozy restaurants perfect after a day outside. With its balance of crisp mountain air, colorful leaves, and small-town charm, Lake Placid delivers a fall weekend that kids and parents alike will remember. Hotels range from $200-$350/night on average in the fall.

Pennsylvania

Jim Thorpe – Nicknamed the “Switzerland of America,” Jim Thorpe is a storybook mountain town that shines in the fall. Families flock here for the Fall Foliage Festival, when the streets fill with craft vendors, live music, kids’ activities, and plenty of festive treats. A ride on the Lehigh Gorge Scenic Railway gives little ones a magical view of the autumn colors, while outdoorsy families can enjoy bike rides along the D&L Trail or hikes in Lehigh Gorge State Park. With its mix of small-town charm, mountain views, and seasonal fun, Jim Thorpe makes a cozy and colorful fall escape for families. Jim Thorpe is mostly rental homes and those average $250-$400/night in the fall.

Hershey – Sweet meets spooky in Hershey, where chocolate and Halloween fun go hand in hand. Hersheypark Halloween and Dark Nights transform the park into a family-friendly Halloween wonderland. During the day, kids can join character dance parties, follow the Trick-or-Treat Trail, and enjoy rides without scares. After dusk, braver families can explore haunted houses and scare zones designed for older kids and adults. ZooAmerica, included with admission, adds animal encounters and nocturnal creature fun, while seasonal snacks—from cider to chocolatey treats—keep everyone smiling. Hershey blends the excitement of an amusement park with the magic of Halloween, making it an unforgettable fall weekend getaway for families with kids of all ages. Hotels range from $150-$300/night on average in the fall.

New Jersey

Cape May – Cape May may be known for summer beach trips, but autumn transforms this Victorian seaside town into a cozy fall getaway. Families can join Halloween Happenings, which includes kid-friendly ghost tours, themed trolley rides, and pumpkin decorating. The Cape May Zoo and surrounding park are favorites for younger children, offering a mix of animals, playgrounds, and fall foliage. Parents will love strolling the streets lined with colorful Victorian homes, browsing boutiques, and enjoying seasonal treats at local cafés. With a slower pace than summer, Cape May in the fall balances festive Halloween fun with laid-back family relaxation. Hotels range from $200-$400/night on average in the fall.

Lambertville – Perched along the Delaware River, Lambertville is a charming small town that pairs historic streets with plenty of autumn fun for families. In fall, the town’s scenic riverfront views are framed by colorful foliage, and families can stroll the walkable downtown filled with sweet shops, cafés, and galleries. Just across the bridge, New Hope, PA joins in the seasonal spirit with pumpkin displays, kid-friendly festivals, and Halloween events—making the two towns a perfect paired getaway. Local farms nearby offer hayrides, apple picking, and corn mazes, while the Delaware & Raritan Canal Towpath provides an easy, stroller-friendly way to take in the crisp fall air. It is mostly rental houses in Lamberville, which range from $300-$500/night, or stay in nearby Ewing in hotels which range from $150-$300/night in the fall.

Delaware

Lewes – Known as the “First Town in the First State,” Lewes is a seaside gem that takes on a cozy, small-town charm in the fall. Families can enjoy quiet days at Cape Henlopen State Park, where bike trails, gentle hikes, and wide beaches offer plenty of space for kids to explore among the autumn colors. The town itself hosts family-friendly festivals like the Boast the Coast Maritime Festival, with boat rides, crafts, and activities by the water, and the popular Sea Witch Festival in nearby Rehoboth Beach adds parades, costumes, and trick-or-treating fun. With ocean breezes, fall festivals, and a slower pace than summer, Lewes makes for a refreshing and family-friendly autumn escape. Hotels are about $200/night in the fall.

Maryland

Annapolis – Maryland’s capital city sparkles in the fall, offering families a perfect mix of waterfront fun, history, and seasonal celebrations. Kids will love exploring the harbor by boat or taking a fall foliage cruise on the Chesapeake Bay, where the autumn colors meet the water. Downtown Annapolis is walkable and lively, filled with sweet shops, cafés, and colonial history at every turn. In October, the Annapolis Boat Shows bring excitement to the waterfront, while pumpkin patches and farms just outside the city offer hayrides and cider treats. With crisp breezes, family-friendly events, and a charming downtown, Annapolis is a fun and easy fall getaway. Hotels range from $250-$600/night on average in the fall.

Thurmont – Nestled near the Catoctin Mountains, Thurmont is small-town Maryland at its fall best. Families flock here for the Catoctin Colorfest, one of the region’s largest fall festivals, featuring hundreds of craft vendors, live music, kids’ activities, and delicious seasonal food. For outdoor adventures, nearby Cunningham Falls State Park offers easy trails, waterfalls, and picnic areas perfect for younger children. Families can also explore local farms for pumpkin picking and hayrides or take scenic drives through Catoctin Mountain Park to soak in the autumn leaves. Thurmont is mostly rental homes which average $250-$400/night in the fall.

Virginia

Williamsburg – Williamsburg shines in autumn, offering a mix of history, nature, and family-friendly seasonal events. At Colonial Williamsburg, kids can explore living history demonstrations and even join Halloween-themed tours designed for younger visitors. Busch Gardens adds extra magic with Howl-O-Scream for older kids and adults, plus The Count’s Spooktacular—a daylight event perfect for younger children with trick-or-treating and dance parties. Families can also enjoy colorful foliage in nearby parks, explore pumpkin patches, and savor fall flavors at local markets. Hotels range from $150-$250/night on average in the fall, and Busch Gardens Williamsburg offers excellent hotel/park packages.

Abingdon – Abingdon is a charming Appalachian town that shines in autumn, offering families the perfect blend of outdoor beauty and small-town warmth. The famous Virginia Creeper Trail is a must—families can rent bikes with child trailers or take short walks along the path, surrounded by colorful mountain foliage. In October, the town hosts harvest festivals with live music, crafts, and kid-friendly activities, while nearby orchards invite families to pick apples and pumpkins. Downtown Abingdon is walkable and full of history, with cozy cafés, candy shops, and the playful Barter Theatre, which often offers family-friendly performances in the fall. Hotels average $100-$200/night in the fall and there are also a good number of rental homes between $150-$300/night as well.

North Carolina

Blowing Rock – Blowing Rock offers storybook mountain views, gentle trails, and a charming small-town atmosphere that feels tailor-made for fall family adventures. Kids will love exploring the historic downtown, hiking short scenic paths, or simply running through colorful foliage along the Blue Ridge Parkway (20-mile section open near town) Blowing Rock escaped Hurricane Helene’s worst, and infrastructure is fully restored with all businesses and roads operational. This makes it a reassuring and delightful option for a fall getaway where seasonal beauty meets safety and accessibility. Hotels range from $250-$500/night on average in the fall.

South Carolina

Greenville – Greenville is a fantastic family destination in the fall, blending outdoor beauty with lively seasonal events. The Fall for Greenville festival fills downtown with music, food, and family fun, while Falls Park on the Reedy and the Swamp Rabbit Trail offer colorful spots for walks, bike rides, and playtime. Families can also enjoy the TD Saturday Market through late October, complete with trick-or-treat fun, or head to nearby farms for pumpkin picking, hayrides, and cider donuts. With its vibrant downtown and cozy seasonal charm, Greenville makes for a memorable autumn weekend getaway. Hotels range from $150-$300/night on average in the fall.

Georgia

Helen – Nestled in the North Georgia mountains, Helen transforms into a storybook Bavarian village each fall, making it a magical spot for families. The town’s alpine charm is enhanced by colorful fall foliage, scenic hikes along the Chattahoochee River, and pumpkin patches perfect for little hands. Kids love the interactive corn mazes, hayrides, and seasonal festivals, while adults can savor local treats and stroll the quaint streets lined with shops and bakeries. With family-friendly Oktoberfest activities in late September through October, Helen combines mountain beauty, festive fun, and a touch of whimsy for an unforgettable autumn getaway. Hotels range from $200-$400/night on average in the fall.

Savannah – Savannah offers a milder coastal fall experience filled with history, charm, and plenty of family-friendly activities. Families can wander through the city’s leafy squares, enjoy carriage rides, or explore the waterfront for crisp river breezes and scenic views. October brings seasonal festivals, Halloween events, and the popular Ghosts and Gravestones Trolley Tour with age-appropriate options for younger kids. Nearby farms and pumpkin patches add classic fall flair, and downtown Savannah’s cafés, ice cream shops, and historic homes make for easy strolls with little ones. Hotels range from $175-$400/night on average in the fall.

Florida

St. Augustine – St. Augustine, the nation’s oldest city, offers families a mix of history, charm, and seasonal fun in the fall. Kids will love exploring the cobblestone streets, Castillo de San Marcos, and the Pirate & Treasure Museum, while parents can enjoy scenic strolls along the waterfront and colorful fall decorations around the historic district. October brings festive events like the Nights of Lights Halloween Festival and family-friendly ghost tours, plus nearby farms and pumpkin patches provide hayrides, cider, and classic autumn treats. Hotels range from $150-$400/night on average in the “fall” – let’s be real. It’s not cold in FL in October.

Orlando – Orlando is a go-to destination for fall family fun, combining theme parks, seasonal events, and outdoor adventures. Walt Disney World, Universal Orlando, and SeaWorld all host spectacular Halloween festivities, from daytime trick-or-treating to themed parades and shows suitable for younger kids. Beyond the parks, families can enjoy pumpkin patches*, corn mazes, and local fall festivals across the city. With endless activities for little ones and adults alike, Orlando makes for a lively, festive, and unforgettable autumn getaway. Hotels average $200-$600/night in the “fall” (again, Orlando is not cold in October usually), and can range from Disney/Universal resorts to independently owned, just depends on what you’re looking for and where you want your home base.

*To be fair, most pumpkins are not grown on farms in FL (yes, there are heat tolerant varieties, don’t come at me). Having grown up in south Florida, pumpkins are usually trucked into church parking lots, but they are still very festive!!

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From spooky lantern tours in Sleepy Hollow to sweet treats in Hershey and colorful mountain drives in North Carolina, the Eastern U.S. offers endless opportunities to celebrate fall and Halloween as a family. Whether your kids love costumes, pumpkin patches, or just a cozy weekend away, these destinations promise fun-filled, memory-making weekends.

Pack your sweaters, grab some cider, and get ready to experience fall magic close to home. 🍁✨

Ready to make your fall family weekend a reality? Contact me today! We can talk locations, hotel options, and additional things to do to make you one easy fall vacation package!