Put on your walking shoes and explore 10 top East Coast locations that are perfect for hosting your next family reunion
Planning a multi-generational reunion can be challenging, but a walkable town makes it simple. These 10 towns offer everything your group needs within steps, including lodging, dining and activities for all ages. From waterfront parks and historic landmarks to kid-friendly museums and local eateries, each town has something exciting for your family.
With no need to coordinate carpools or worry about parking, these historic towns promise less stress and more quality time. The perfect blend of simplicity, character and convenience, these walkable towns in the Eastern US can turn your reunion into a meaningful and memorable experience for the entire family.
Check out each town’s walk score to choose the best destination for your family.
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S&P Oyster Restaurant & Bar. Photo credit: Greater Mystic Chamber of Commerce Facebook
1.) MYSTIC, CT
Downtown Mystic is an excellent, walkable waterfront district saturated with historic charm, offering something for every age. Located alongside the Mystic River, the town combines shopping, dining, and attractions all in one convenient location.
Families can enjoy over 80 local shops and galleries, featuring a diverse range of products, from gifts and books to arts and antiques. Foodies will love maritime-inspired restaurants like S&P Oyster Restaurant & Bar and The Engine Room, as well as sweet shops like Anchor Cafe & Sweets.
Kids, parents and grandparents alike will enjoy visiting the Mystic Museum of Art, having riverside picnics at Mystic River Park and watching the famous Bascule Bridge in action.
Stay at the Mermaid Inn or The Whaler’s Inn Hotel of Mystic, just a 10-minute stroll away from downtown.
Stockbridge, MA, Main Street. Photo credit: Visit Stockbridge Massachusetts Facebook
2.) STOCKBRIDGE, MA
Nestled in the Berkshire Mountains lies Stockbridge—a town known for cultural attractions, historic architecture and idyllic scenery.
Stroll on the town’s wide, brick sidewalks to experience traditional New England charm. Explore Main Street and grab a bite or a drink to sip at places such as The Lost Lamb or Main Street Cafe. Enjoy some sweets at Peace Love & Chocolate.
Journey back in time with the whole family at the Mission House—the former home of an 18th-century missionary converted into a Mohican Native American museum full of artifacts. Continue the learning experience by stopping in the non-profit museum, Merwin House.
Stay at The Red Lion Inn, an inn that features a famous front porch that offers the perfect spot to sit, sip and enjoy the picturesque views.
Wander down quaint Portsmouth Main Street. Photo credit: Go Portsmouth NH Facebook
3.) PORTSMOUTH, NH
Packed with hands-on history and kid-friendly charm, Portsmouth is an ideal destination for families seeking an easy-to-explore place.
Start at the Strawbery Banke Museum, where kids and adults can tour 39 historic homes, try traditional crafting and explore Portsmouth through time. Steps away sits the Moffatt-Ladd House & Garden, offering a leisurely stroll filled with history and horticulture.
For a more interactive experience, consider going on a Portsmouth Scavenger Hunt. Captain Jack’s Magical Fountain tour—designed specifically for families—is a 0.6 mile, stroller-friendly and mostly wheelchair accessible adventure through downtown’s historic landmarks.
Take a picnic with waterfront seats in Prescott Park. Lounge and enjoy the views, or take a stroll five minutes away to catch a performance at the Seacoast Repertory Theatre.
Stay nearby at the Davenport Inn, Sheraton Portsmouth Harborside Hotel or The Sailmaker’s House for a conveniently located hotel.
Annapolis, Maryland offers history along every cobblestone street. Photo credit: Adam Brockett
4.) ANNAPOLIS, MD
Historic downtown Annapolis preserves 18th-century charm within a 21st-century neighborhood. Look in any direction on Main Street to find activities that will pique the interest of anyone in your family.
Catch views of the Chesapeake Bay or play a game with the family, spotting Midshipmen in dress whites. Take a leisurely walking tour with Annapolis Ghost Tours to experience a journey through Annapolis’ spooky history.
Annapolis EvenTours is a perfect option for families looking to ride around town—whether to accommodate children or those with mobility issues. You’ll see historic landmarks like the U.S. Naval Academy and the Maryland State House while learning about the town’s role in shaping America.
Stop by local favorites like O’Brien’s Oyster Bar & Seafood Tavern for fresh fish or Luna Blu for mouthwatering Italian cuisine. Wrap up the night with a sweet treat from Kilwin’s Chocolates & Ice Cream.
Stay at History Inns of Annapolis or Flag House Inn for a convenient location that places your family in the center of the action, making reunions fun and stress-free.
5.) PHILADELPHIA, PA
Elfreth’s Alley. Photo credit: Visit Philly Facebook
Whether pushing a stroller or walking with grandparents, Philadelphia is one of the most walkable cities in the country—perfect for multigenerational reunions. Top spots are located close together, easy to reach on foot for all ages.
Stay in the Historic District at places, such as the Kimpton Hotel Manco or the Wyndham Philadelphia, to be steps away from family-friendly activities like the Liberty Bell, Independence Hall or the Museum of Illusions. Stroll down historic Elfreth’s Alley for unique photo ops.
Franklin Square and the Please Touch Museum are perfect for kids, while older generations will appreciate the history at sites like the Museum of the American Revolution.
Grab casual bites throughout the city at places like the Reading Terminal Market (featuring over 70 family-owned, small businesses), or Pizzeria Stella, and finish up the day with ice cream from local-favorite Annabelle’s Natural Ice Cream.
6.) ST. MICHAELS, MD
St. Michael’s is a walkable seaside escape. Photo credit: St. Michaels Facebook
St. Michaels is a walkable, family-friendly town ideal for a stress-free reunion located on the banks of Maryland’s Eastern Shore. With everything located within a few scenic blocks, families can explore together at a relaxed pace.
Start at the Chesapeake Bay Maritime Museum to experience exhibits, guided tours and even boat rides for the whole family. The historic 1879 Hooper Strait Lighthouse is just a three-minute walk away and offers an engaging experience for all ages with a sea hatch and lookout.
Enjoy a waterside meal at The Crab Claw, or check out the vibes at Carpenter Street Saloon—a local pub with pool tables, live music and a fascinating model train. For a midday break, check out Justine’s Ice Cream Parlour, a charming, old-fashioned ice cream shop with a variety of flavors.
If you want to spend the day outside, pack a meal and share it with your family at the picnic tables at Hollis Park. A perfect spot for the whole family, the park features boardwalks, benches and a playground for the kids.
Stay within walking distance of all the action at the Inn at Perry Cabin, The Wildset Hotel or St. Michaels Harbour Inn.
7.) ST. AUGUSTINE, FL
Take a guided walking tour of historic St. Augustine. Photo credit: St. Augustine Attractions Association Facebook
St. Augustine is a walkable gem for multigeneration fun, blending history with quirky attractions—all easily explored on foot.
Explore the Castillo de San Marcos, where self-guided tours lead you and your family from the drawbridge to the gundeck, complete with views of Matanzas Bay. Steps away is the St. Augustine Pirate & Treasure Museum, an interactive adventure with scavenger hunts and pirate artifacts.
A must-see is the offbeat Ripley’s Believe It or Not!, packed with both oddities and history, like shrunken heads and rare animal skeletons. Let the kids run around at Project SWING Park, located near the iconic Bridge of Lions, which is sure to fascinate older adults.
When hunger strikes, head to Georgie’s Diner, a nostalgic ’60s spot that serves Greek and American favorites. Schmagel’s Bagels—a casual, counter-serve shop serving New York-style bagels and sandwiches—is another excellent spot to try.
Stay on the water at the Hilton St. Augustine Historic Bayfront or enjoy timeless charm at the Renaissance St. Augustine Historic Downtown Hotel—both within walking distance of all St. Augustine has to offer.
8.) SAVANNAH, GA
Historic River Street in Savannah, GA. Photo credit: Visit Savannah Facebook
Downtown Savannah is known for its ease for pedestrians. With mossy, oak-lined streets, Savannah is perfect for strolling with the entire family.
A must-visit is Forsyth Park. This 30-acre green space begs for your family to lounge and play in, with basketball and tennis courts, winding paths to meander on and a beautiful historic fountain to admire. Come on Saturday to see some local artisans!
Visit the famous City Market, a hub for popular restaurants, live performances, unique shopping, museums and more. Nestled between Franklin and Ellis Squares, the market has been the heart of downtown since 1755.
Sweet treats like Byrd’s Famous Cookies or Leopold’s Ice Cream provide the perfect pick-me-up during a day of exploring the city’s cobblestone streets along famous River Street. For creative fun, head to the Artzeum, a hands-on art space where kids can create their own masterpieces.
After a day of sightseeing, unwind for the night at family-friendly hotels like The Alida in Savannah or The Marshall House, both of which offer Southern charm and easy access to the city.
Angel Oak in historic Charleston, SC. Photo credit: Visit Charleston, SC Facebook
9.) CHARLESTON, SC
Charleston is a fantastic destination thanks to its charm, history and walkability. The Historic District, specifically, is flat, compact and easy to explore on foot.
Stroll along Waterfront Park, a serene venue to soak up the sun with picturesque views of Charleston Harbor and the Cooper River. Experience the Waterfront Swings or walk south and take a picture at the Pineapple Fountain. Visit the iconic Angel Oak, a Lowcountry treasure that’s estimated to be between 400 and 500 years old!
Delve into history by walking down Rainbow Row—a cluster of 13 pastel-painted Georgian-style rowhouses that promises to catch the attention of the entire family. Visit the Gibbes Museum of Art, which showcases over 10,000 works that preserve Charleston’s rich cultural heritage.
For a quick bite to take on the road, stop in Queen Street Grocery—an old-fashioned grocery and cafe known for its hot-pressed sandwiches, crepes, and smoothies. For a sit-down eatery, try Frannie & The Fox, a relaxed Italian restaurant with pizza that will please the whole family.
Stay at The Elliot House Inn or Market Pavilion Hotel to be steps away from activities, no need to drive!
Living history for groups at Colonial Williamsburg. Photo credit: Colonial Williamsburg Facebook
10.) WILLIAMSBURG, VA
Williamsburg is the ideal spot for walkable family reunions with engaging destinations.
Start at Colonial Williamsburg’s Merchants Square, where over 40 specialty shops and restaurants within historic buildings create a nostalgic setting for families to explore. Kids and adults alike love carriage rides, the Kimball Theater, and immersive historical experiences.
Just a short walk away, Palace Green—a history museum on Georgian grounds—offers a vast lawn space to lounge on, gardens to wander through, and over 89 18th-century buildings to admire. Another relaxing area is the Sunken Garden, located on William & Mary College’s Old Campus. This spot is an ideal location for picnics and family photos.
Enjoy outdoor seating and casual dining at Rick’s Cheese Steak Shop, a local favorite with family-friendly surroundings. Around the corner sits The Bake Shop for those looking for sweet coffee, baked goods and light bites.
Lodging options like the Armistead House or Fife and Drum place you in the heart of town, making the day easy to navigate.
START PLANNING TODAY
Walkable towns aren’t just scenic—they’re a game-changer for planning smooth, enjoyable family reunions. With everything from hotels and restaurants to parks and museums, groups can focus on memory-making instead of managing transportation.
These destinations take the stress out of multi-generational group travel and offer a relaxed pace, magnificent surroundings and easy access to activities. Whether exploring cobblestone streets, historic districts or waterfront boardwalks, walkable towns allow your family to truly connect.
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By Madelyn Bugai, Contributing Writer
