Three Generational Travel in Connecticut Last Updated: November 2021

After so many of us missed beloved family events and holiday parties with loved ones, we’re ready to make up for lost time. And nothing says quality time like traveling together! From cozy accommodations and delicious dining to active adventures, arts & culture, outdoor fun, and beyond, we’ve gathered ways to get away with grandparents, grandkids, and everyone in between.

Fairfield County
Litchfield Hills
Greater Hartford
Greater New Haven
Northeast Corner
Mystic Country
Reunite
More Ideas

Fairfield County

Stay

In Fairfield County, get away together with Hampton Inn Shelton’s Family Fun Staycation package. In addition to a spacious room, you’ll enjoy a hot breakfast buffet, indoor heated pool, $20 to SportsCenter of Connecticut, a large cheese pizza and more. Or enjoy the historic character of the Circle Hotel in Fairfield. Grandma will enjoy the comfort and the kids will love the pool and bike rentals.

Eat

Stop for a bite at Little Pub in Stratford, Fairfield, Greenwich, or Wilton for a rustic neighborhood gathering place and dishes for the young and the young at heart. Parents and grandparents will love classics like fish ‘n chips and BLTs or foodie twists on entrees such as meatloaf grilled cheese, while the youngins will enjoy the kid’s menu or variety of mac ‘n cheese dishes. In Norwalk, devour tavern favorites and a great kid’s menu at O’Neill’s Pub and Restaurant, or enjoy over 50 flavors of ice cream at Wells Hollow Creamery in Shelton.

Play

Travelers of all ages will love making animal friends at the Maritime Aquarium at Norwalk or Connecticut’s Beardsley Zoo in Bridgeport or making outdoor discoveries together at Webb Mountain Discovery Zone in Monroe. Depending on the season, enjoy family-friendly events like maple sugaring, tomato tasting, fall farm days, pancake breakfasts, and opportunities to see farm animals at Ambler Farm in Wilton. At Jones Family Farms in Shelton, the kids can enjoy berry and pumpkin picking as well as many acres to roam, while older family members can sip wine in the historic barn of Jones Family Winery.

Litchfield Hills

Stay

Escape as a family to Interlaken Inn in Lakeville and discover a family-welcoming, pet-friendly lakeside resort with 30 acres of gardens, a spa, and countless recreational offerings for all ages. Stay at the Doubletree Hilton in Bristol for great rates, comfort, and an indoor pool the kiddos will appreciate. Or if you’ve got an adventurous grandparent in the family, try Club Getaway for a family summer camp experience filled with active adventure during the summer months.

Eat

For great family dining, try Jesse Camille’s in Naugatuck or find fantastic flavors and kid’s menus at San Marino Restorante Italiano in Waterbury and Market Place Tavern in Litchfield. Or find sweets the whole family will love at Denmo’s Dairy & Snack Bar or Arethusa Farm – because who doesn’t love ice cream?

Play

Get creative with all generations when you paint pottery, make candles or soap, and more at The Pottery Factory in Brookfield, or get artsy the sweet way at Fascia’s Chocolates’ Make-A-Bar experience in Waterbury. If your oldest family members are still active, embark on adventure at Main Stream Canoes & Kayaks in New Hartford, Bicycle Tour Company in Kent, or try Guided Flyfishing Trips with Housatonic River Outfitters in Cornwall. Another memorable outing for all ages is a trip to the New England Carousel Museum in Bristol. Parents and grandparents will love learning the history and connecting to childhood wonder, while the kids will have a blast on the indoor carousel.

Greater Hartford

Stay

At the Marriott Hartford Downtown, get the Science Center Discovery package for free tickets to the Connecticut Science Center, discounts to hotel restaurant Vivo Seasonal Trattoria, and more. Book an overnight by the sea at Water’s Edge Resort & Spa, where older family members will appreciate fine dining, a full-service spa, and lovely scenic accommodations, and the youth can make a splash in the pool or build castles on the beach. If you have a big family, rent Saybrook Point Resort & Marina’s guest houses for a trip that’s merrier with more!

Eat

One fun way to satisfy the tastebuds of all ages is to take a family trip to a food hall. At Parkville Market in Hartford or Essex Public Food Hall you’ll find flavors from a variety of cultures and even foodie favorites like fried chicken and gourmet grilled cheese booths – there’s sure to be something for grandpa and the kiddos alike! In Plainville, try nationally renowned buffalo wings and a great kid’s menu at J. Timothy’s Taverne, or find more options for the kids (and parents too) at Lenny & Joe’s Fish Tale in Westbrook, Max Burger Bar in West Hartford, or Max A Mia Ristorante in Avon, which also offers group dining options for large groups.

Play

In Hartford County, there are plenty of spots to get out with the extended family. Pick your own produce at Rose’s Berry Farm in South Glastonbury or Clark Farms at Bushy Hill Orchard in Granby, meet farm animals at Ray of Light Farm in East Haddam or Flamig Farm in Simsbury, or buy peanuts and cracker jacks when you see The New Britain Bees or the Yard Goats play ball.

Another great way to connect all three generations is to make discoveries together at spots like the New England Air Museum in Windsor Locks or the Connecticut Trolley Museum in East Windsor. Or perhaps you’ll solve interactive puzzles together at escape rooms such as Adventure Rooms in Middletown or Team vs. Time in Berlin.

Greater New Haven

Stay

Enjoy enough room for the whole family when you stay in The Homewood Suites by Hilton in Wallingford or get comfort you’ll appreciate and an indoor pool for the kids at SpringHill Suites by Marriott in Milford. For a shoreline escape, breathtaking sunrises, and plenty of family-friendly amenities, try the Madison Beach Hotel. Staying extra long? Book a comfortable stay at the New Haven Village Suites and enjoy the conveniences of a hotel with the comforts of home.

Eat

All members of the family will appreciate the history (and delicious flavors) of a New Haven pizza tour. Sample the award-winning slices of Frank Pepe Pizzeria Napoletana, Sally’s Apizza, Modern Apizza, and beyond – and vote to see if the family has a favorite. For more foodie history the family will love, try the home of the hamburger: Louis’ Lunch. In the warmer months, enjoy a unique outdoor dining experience at The Place in Guilford, or grab a cone at Ashley’s Ice Cream. And if kitties are loved by the grandkids and grandparents alike, stop in at Mew Haven Cat Café for coffee, baked goods, and a visit with adorable cats.

Play

Bring out every family member’s inner child when making fun discoveries at the PEZ Visitor Center in Orange, The Shore Line Trolley Museum in East Haven, or the Barker Character, Comic & Cartoon Museum in Cheshire. For outdoor fun, visit Gouveia Vineyards, Paradise Hill Winery, or Bishops Orchards Farm Market & Winery – the older family members can sit back with a glass of wine while the kids enjoy the gorgeous grounds. In the spring, summer and fall, a trip to Lyman Orchards is great for family bonding. Enjoy pick-your-own produce, a corn maze, and a large farm market grandma and grandpa are sure to love.

Northeastern Corner

Stay

Book a night at the Comfort Inn & Suites in Dayville or The Inn at Storrs and enjoy breakfast each morning and an indoor pool where the youngsters can make a splash. Or take advantage of the Quiet Corner’s stunning scenery and stay in the cottage at Tyrone Farm in Pomfret Center, which offers a full kitchen, three bedrooms, wood stove, screened-in porch of the master suite, and plenty of comfort for all.

Eat

When you dine at The Courthouse Bar & Grille in Putnam, you’ll enjoy delicious food in a repurposed space filled with history plus a kid’s menu – named Juvenile Hall – with all the kiddy favorites. You’ll also discover great menus at Vanilla Bean Cafe in Pomfret and Hank’s Restaurant in Brooklyn, which has award-winning family style food and has even been prized with the best kid’s menu.

Play

Connecticut’s Northeast Corner is a great area to get outdoors with all three generations of your family. Take a leisurely stroll on the Putnam River Trail, which boasts beautiful foliage if you go in the fall. Or visit Woodstock Orchards, Fort Hill Farms, or Buell’s Orchard in Eastford. For a breathtaking memory the family will never forget, take a hot air balloon ride at Connecticut Voyager Balloons in Woodstock. If your family shares a love of motor vehicles, visit Thompson Motor Speedway for racing events and a golf club.

Mystic Country

Stay

If you’re traveling in Mystic Country, make the most of the casinos and stay over with the Family Fun for All package at Mohegan Sun, or book a night and explore all that’s waiting at Foxwoods Resort Casino – you’re sure to find plenty of family fun. Another great spot to stay is downtown Mystic, where the views, activities and downtown charm will be adored by grandparents and grandchildren alike. Book a night in the Steamboat Inn, Harbor View Landing, or the Mystic Marriott Hotel to be near this popular spot.

Eat

Grab a pizza with everyone’s favorite toppings and more at Ocean Pizza Restaurant in New London, or find everyone’s breakfast favorites all day long at Mystic Diner. In downtown Mystic, enjoy a nice meal at Oyster Club or grab a slice at the famous Mystic Pizza, then head to Mystic Drawbridge Ice Cream or Sift Bake Shop for dessert. For great kid’s menus and delicious dishes for all, try Olde Tymes Restaurant in Norwich or Chester’s Barbecue in Groton, which also offers family-style meals.

Play

Grandma and Grandpa will love making discoveries (and great memories) with the kids at Mystic Aquarium and Mystic Seaport Museum, or strolling through the shops in Olde Mistick Village. Plus find even more to discover at the Custom House Maritime Museum in New London or New England Science & Sailing in Stonington. At The Shops at Nature’s Art Village, you’ll find joy for all ages from antiquing and jewelry shops to mini golf and fossil finding. And on a rainy day, solve riddles as a family at Lost Totem Escape Trail in Mystic or MindBreak Escape Rooms in Norwich.