With fresh-from-the-ocean seafood and five James Beard Award-winning chefs, Portland, Maine, is renowned as a foodie city that brings legions ready for a feast. But this culinary mecca also brews up plenty to pair your plates with, and the Brew Bus is a popular go-to for bachelorettes and couples’ weekends. You can have some of the same fun small-scale, though, and hit up some of the same hot spots near Rising Tide Brewery, where there are food trucks and lawn games outside (along with some doggie watering holes) and Maine Craft Distilling just next door. Check out the blueberry moonshine, made with local fruit, rum, whiskey or gin.

Photo: Napa Valley Wine Train
Kids love trains and parents love wine, so what’s not to love about the Napa Valley Wine Train? Aboard Pullman cars from the early 1900s, a short attention span-friendly itinerary zips past scenic vineyards for an on-and-off adventure. Children 12 and under can have lunch at kid-friendly prices (albeit with apple juice only) while Mom and Dad enjoy an included vintage with all three courses. Everyone gets to enjoy visits to local wineries with samplings or the chance to get out some energy exploring between the vines. There’s even a special Santa wine train at Christmas.

Porto Wine Tasting. Photo: Carley Thornell
Think New England’s craft breweries are the only spirits worth raising a glass to? Think again. The Coastal Wine Trail connects charming villages and historic cities all close to the Atlantic Ocean (with a southeastern facing coastline that captures the warm gulf stream waters in the summer and fall). Fourteen wineries owned and operated by local families include Cape Cod through the southern coast of Massachusetts, coastal Rhode Island and into coastal Connecticut, producing 50 vintages. Kids can run through the fields of vines and blow off some energy, or play lawn games like cornhole at Newport Vineyards in Rhode Island. Nearby, kids are welcome at Carolyn’s Sakonnet Vineyard, which hosts Halloween costume parties and weekly theme tastings, and is dog-friendly.
Portland, Oregon’s, hipster vibe always appeals to a youthful population, but that also includes its pubs, many of which are kid-friendly even if they’re under 21. Zoiglhaus and Caldera Public House even offer kids’ toys and a play area. Most — including the multiple locations of Rogue, Lucky Lab and McMenamins — include family-friendly menu options like burgers, sod, and mac and cheese (and high chairs!); and staying true to Portland’s reputation as a foodie city, Ground Breaker Brewing even has an almond butter and blackberry jelly sandwich.
Williamsburg Tasting Trail serves up craft brews and local wines with a side of history. At 8 Shires, American Heritage spirits offer bourbon and gins made using 18th-century recipes and techniques with Virginia grains and rum is made with molasses. Virginia Beer Company (one of several craft breweries) has a family-friendly taproom that’s pet- and kid-friendly, with an outdoor beer garden with weekly food trucks, live music and events. And the Colonial Wine Trail features four wineries within an hour’s drive of Williamsburg. (Make sure you plan ahead so there’s no hint of a hangover for a day at Busch Gardens!)

Porto. Photo: Carley Thornell
What kid doesn’t like a cave to explore in? Porto’s waterfront may be a UNESCO site filled with lots to see (bridge-jumping divers) and do (cruises and a funicular), but there’s plenty of fun to be had at Port wine cellars, which offer several short tours in English a day. Clustered in the same neighborhood — Vila Nova de Gaia — it’s easy for little legs to walk to each if Mom and Dad want to enjoy more than one. Croft and Taylor are family-friendly faves.
With group seating, bocce ball, horseshoes and ladderball, Larson Family Winery lives up to its name. In its fifth generation as a family business, the Larsons manage more than 600 acres of Sonoma’s tastiest grapes and an education-focused wine program that welcomes even the youngest of vintners — groups from the local middle and high schools to learn about horticulture.
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