# Fall Trips For Guys Who Like Beer And Wine *By James Hills — Updated October 2026* Written by: [James Hills](https://menwhoblog.com/james-hills.html) Last Updated: 05 October 2026 New!Hits: 39Reading time: 09:54 Fall is harvest season in wine country and festival season in beer towns, which makes it the best time of year for a tasting weekend with the guys or with your wife. These 12 destinations run from bourbon in Frankfort, Kentucky and pinot in Oregon's Willamette Valley to Beer City USA in Grand Rapids, and several of them cover beer, wine and spirits in the same place ... making it the perfect trifecta of enjoying the spirit of fall! **Featured Destinations****Who Drives, And Other Tasting Weekend Logistics****Article Index** - **Frankfort, Kentucky -** six distilleries in town and the rest of the Kentucky Bourbon Trail within an hour. - **Hudson Valley, New York -** the Shawangunk Wine Trail, a distillery brunch and rooftop football at a brewery. - **Willamette Valley, Oregon -** small wineries where the person pouring is often the winemaker. - **Portland, Maine -** Allagash, a Casco Bay ferry and lobster rolls in a compact downtown. - **Charlottesville, Virginia -** an e-bike wine tour led by a sommelier in the Blue Ridge foothills. - **California's Central Coast -** Santa Barbara, the Santa Ynez Valley, Santa Maria and Paso Robles, without the attitude. - **Denver, Colorado -** a big craft beer city with a themed hotel downtown. - **Bend, Oregon -** a brewery town with a David McLay Kidd golf course on the edge of the forest. - **Asheville, North Carolina -** a walkable brewery district and Blue Ridge Parkway color. - **Grand Rapids, Michigan -** Beer City USA and a brewery passport to fill. - **Walla Walla, Washington -** more than 100 wineries around a small downtown. - **St. Joseph, Michigan -** Lake Michigan Shore wine country on a beach town weekend. The details that ruin a tasting weekend are almost never about the wine or the beer, so settle them before you leave. - **Decide on the driver before the first stop -** a hired driver, a guided tour or a walkable base like Santa Barbara's Funk Zone means nobody has to sit out. - **Cap it at three or four stops a day -** tasting pours add up, and the fourth winery never gets the attention the first one did. - **Eat a sit-down lunch between stops -** crackers at the tasting bar are not a meal, and food slows down the afternoon pours. - **Ask whether the tasting fee is waived with a purchase -** many wineries credit the fee if you buy a bottle, which changes the math on a budget. - **Plan how the bottles get home -** wine can't go in a carry-on over 3.4 ounces, so check a padded wine bag or have the winery ship to your house. 1. [Frankfort, Kentucky - Home Base For The Bourbon Trail](https://menwhoblog.com/fall-beer-and-wine-trips-for-guys.html#frankfort-kentucky-home-base-for-the-bourbon-trail) 2. [Hudson Valley, New York - A Wine Trail And Rooftop Football](https://menwhoblog.com/fall-beer-and-wine-trips-for-guys.html#hudson-valley-new-york-a-wine-trail-and-rooftop-football) 3. [Willamette Valley, Oregon - Tasting With The Winemaker](https://menwhoblog.com/fall-beer-and-wine-trips-for-guys.html#willamette-valley-oregon-tasting-with-the-winemaker) 4. [Portland, Maine - Allagash, Lobster Rolls And Casco Bay](https://menwhoblog.com/fall-beer-and-wine-trips-for-guys.html#portland-maine-allagash-lobster-rolls-and-casco-bay) 5. [Charlottesville, Virginia - Wine Country By E-Bike](https://menwhoblog.com/fall-beer-and-wine-trips-for-guys.html#charlottesville-virginia-wine-country-by-e-bike) 6. [California's Central Coast - Santa Barbara To Paso Robles](https://menwhoblog.com/fall-beer-and-wine-trips-for-guys.html#californias-central-coast-santa-barbara-to-paso-robles) 7. [Denver, Colorado - A Craft Beer Capital With A Playful Hotel](https://menwhoblog.com/fall-beer-and-wine-trips-for-guys.html#denver-colorado-a-craft-beer-capital-with-a-playful-hotel) 8. [Bend, Oregon - A Brewery Town With A Golf Course](https://menwhoblog.com/fall-beer-and-wine-trips-for-guys.html#bend-oregon-a-brewery-town-with-a-golf-course) 9. [Asheville, North Carolina - Breweries And The Blue Ridge Parkway](https://menwhoblog.com/fall-beer-and-wine-trips-for-guys.html#asheville-north-carolina-breweries-and-the-blue-ridge-parkway) 10. [Grand Rapids, Michigan - Beer City USA](https://menwhoblog.com/fall-beer-and-wine-trips-for-guys.html#grand-rapids-michigan-beer-city-usa) 11. [Walla Walla, Washington - More Than 100 Wineries Around A Small Downtown](https://menwhoblog.com/fall-beer-and-wine-trips-for-guys.html#walla-walla-washington-more-than-100-wineries-around-a-small-downtown) 12. [St. Joseph, Michigan - Lake Michigan Shore Wine Country](https://menwhoblog.com/fall-beer-and-wine-trips-for-guys.html#st-joseph-michigan-lake-michigan-shore-wine-country) 13. [How To Plan A Tasting Weekend That Works For Everyone](https://menwhoblog.com/fall-beer-and-wine-trips-for-guys.html#how-to-plan-a-tasting-weekend-that-works-for-everyone)[Match The Trip To Who's Coming](https://menwhoblog.com/fall-beer-and-wine-trips-for-guys.html#match-the-trip-to-whos-coming) 14. [Book The One Thing That Sells Out](https://menwhoblog.com/fall-beer-and-wine-trips-for-guys.html#book-the-one-thing-that-sells-out) 15. [Mix In Something That Isn't A Tasting](https://menwhoblog.com/fall-beer-and-wine-trips-for-guys.html#mix-in-something-that-isnt-a-tasting) 16. [Join The Wine Club Only If You'll Drink It](https://menwhoblog.com/fall-beer-and-wine-trips-for-guys.html#join-the-wine-club-only-if-youll-drink-it) After years of planning fall weekend trips around breweries, distilleries and tasting rooms, I've found that the best ones give the beer guy and the wine guy a reason to be in the same town, which is why the Hudson Valley, Charlottesville, Southwest Michigan and the Central Coast of California are the easiest sell to a group of guys with mixed tastes. It also makes it easy for families since most wineries and breweries are pretty family-friendly, with activities for kids as well as mom and dad. If one of you is still learning your way around a wine list, our guide to [tasting skills that transfer from whiskey to wine](blog/virtual-wine-tasting-with-cameron-hughes-of-de-negoce.html) is a good place to start before you go. ### I Tried Cellular At Sea Cruise+ On Norwegian Getaway A hands-on review of the Cellular At Sea Cruise+ service on Norwegian Getaway, useful for cruisers deciding whether to stay connected at sea. MenWhoBlog [Read More](https://ads.flowmediamarketing.com/go/m4kEYSSNOg30EMMg_qaAKQ.377) ### Why Carnival Splendor Is a Great Choice for a Family Alaska Cruise Our family just returned from our first Alaskan cruise. And it was one of the best vacations we�ve ever taken. On board were myself, my wife, our three kids (aged 11, 12, and 13), and my mother-in-law. Our cruise was a 7-day adventure from Seattle, Washington to three ports of call in Alaska, one in Canada, and the spectacular Tracy Arm Fjord. This was, coincidentally, not our first cruise, but was our first family cruise with everyone on board. MenWhoBlog [Read More](https://ads.flowmediamarketing.com/go/m4kEYSSNOg30EMMg_qaAKQ.2459) ### How to Plan a Caribbean Golf Trip That Will Make The Guys That Didn't Join You Jealous Planning a Caribbean guys golf trip: which courses justify the flight, what all-inclusive covers, and how to keep a mixed-handicap group happy. ManTripping [Read More](https://ads.flowmediamarketing.com/go/m4kEYSSNOg30EMMg_qaAKQ.2156) Promoted by FlowAds ## Frankfort, Kentucky - Home Base For The Bourbon Trail [Frankfort](https://visitfrankfort.com/), Kentucky's state capital, sits on the Kentucky River in the middle of the state, less than an hour from both Lexington and Louisville, and it's home to six distilleries of its own. Buffalo Trace is the famous one, and its tours fill up months in advance, so reserve that first. The others in Frankfort and Franklin County are more likely to take walk-ins, and Kentucky Bourbon Trail distilleries like Woodford Reserve in Versailles and Four Roses and Wild Turkey in Lawrenceburg are within about half an hour, so Frankfort works as a less expensive home base for a Kentucky Bourbon Trail guys trip. Plan on two distilleries a day and hire a local driver. The town gives you more than bourbon. Kentucky River Tours runs the country's only boat-based bourbon tour through November, Canoe Kentucky rents boats for the river and Elkhorn Creek, and Daniel Boone's grave sits on a bluff above the river in Frankfort Cemetery. At night, downtown runs from House of Commons: A Bourbon Library to the river patios at Bourbon on Main and Doc Crow's Social, and the beer drinker in the group has local breweries and taprooms to work through. September is Bourbon Heritage Month, and there's a free downtown trolley. ## Hudson Valley, New York - A Wine Trail And Rooftop Football About 90 minutes north of New York City, the stretch of the Hudson Valley from Poughkeepsie to New Paltz packs wineries, distilleries and hiking into a 30-minute radius of [The Heartwood at Vassar](https://theheartwood.com/), a good base for a newly married couple or a group of guys. The Shawangunk Wine Trail links 13 wineries, including Robibero Winery, Benmarl Winery and Quartz Rock Vineyard and Cider House, and September and October bring grape stomps and harvest festivals. The beer and whiskey side is just as strong. Start a Sunday with brunch and a distillery tour at The Hudson House Distillery, get pizza and a pint at Mill House Brewing, then watch football from the rooftop at Zeus Brewing Company. Walk off Saturday on the Walkway Over the Hudson, a 1.28-mile pedestrian bridge high above the river, ten minutes from the hotel, with the leaves turning on both banks. ## Willamette Valley, Oregon - Tasting With The Winemaker Oregon's Willamette Valley has more than 700 wineries, and most of them are small, so it's not unusual to taste with the owner or the winemaker, the way you can at JL Kiff Vineyard, Compris Vineyard or Bells Up Winery. The valley holds 11 smaller AVAs, and a short drive into the hills leads to view-heavy tasting rooms like Alloro Vineyard and Domaine Divio. [Chehalem Ridge Bed & Breakfast](http://www.chehalemridge.com/) in Newberg sits 1,000 feet up Chehalem Mountain with five guest rooms and a chef-innkeeper cooking a three-course breakfast, a strong pick for a couple's wine weekend that doesn't need a luxury resort price. September is the driest month for a visit, October is still good, and by November the crowds thin out along with the sunshine. Between tastings, hike the waterfalls at Silver Falls State Park or play Chehalem Glenn Golf Course, built on sand so it drains fast after fall rain. The James Beard-nominated Painted Lady and Rosmarino Osteria Italiano cover dinner in Newberg. ## Portland, Maine - Allagash, Lobster Rolls And Casco Bay Portland, Maine pairs peak foliage with a food and craft beer scene you can cover on foot. Allagash Brewing Company is the tasting-room stop the beer drinker will want, lobster rolls and oysters cover the rest of the group, and a ferry through Casco Bay or a walk along the Eastern Promenade shows off the coast in fall color. [The Westin Portland Harborview](https://www.marriott.com/en-us/hotels/pwmwi-the-westin-portland-harborview/overview/) keeps the itinerary simple: its restaurant, Congress Squared, runs a happy hour with drinks under $10 and Football Sunday specials, and the rooftop bar, Top of the East, brings DJ sets and a Halloween party. Fall is also the start of hockey season, and a Maine Mariners game is a lively local night out. ## Charlottesville, Virginia - Wine Country By E-Bike The Charlottesville area is one of the best-known wine regions on the East Coast, and September and October are harvest season, with the summer humidity gone. The best way to see it with a group is on an e-bike tour from [Shifting Gears Travel](https://www.sgtrips.com), led by sommelier and guide Jeff Dion: rolling hills with views toward the Blue Ridge, two winery visits, a vineyard walk and a gourmet lunch, with the motor handling the climbs so the tasting stays the focus. Spend the next morning on the James River in Scottsville with the James River Batteau Company, which runs trips on a replica of the flat-bottomed boats that once hauled cargo on the river. For dinner, Selvedge Brewing pours its own beer with a bar menu from chef Tucker Yoder, and the Boar's Head Inn is a central base with its own golf course. On Sunday, grab a breakfast sandwich to go at Bodo's Bagels. ## California's Central Coast - Santa Barbara To Paso Robles My honest take on California wine country: the Central Coast is more relaxed, less expensive and more fun than the better-known regions to the north and south, and it's often more welcoming to families too. [Santa Barbara](https://santabarbaraca.com/) is the easy start, with the Urban Wine Trail running on foot through the Funk Zone, from Santa Barbara Winery to Margerum and Fox Wine Co., and Figueroa Mountain Brewing and Institution Ale showing games and pouring local for the beer drinkers. October is shoulder season, with rates below summer and the weather usually in the 70s. Inland, the Santa Ynez Valley has dozens of tasting rooms in small towns like Los Olivos, and Santa Maria is the home of Santa Maria-style tri-tip barbecue. Keep going up the coast, and [Cambria](https://visitcambriaca.com/) makes a strong base for Paso Robles, about 30 minutes inland, where October is Harvest Wine Month and the winery hopping mixes easily with breweries, distilleries, and barbecue. Oceanpoint Ranch on Moonstone Beach has fire pits and big lawns built for a group. Cambria's Scarecrow Festival fills the town with more than 200 scarecrows through October, and Hearst Castle and the elephant seals at Piedras Blancas are a short drive north on Highway 1. ## Denver, Colorado - A Craft Beer Capital With A Playful Hotel Denver is one of the country's biggest craft beer cities, and it hosts the Great American Beer Festival, usually in early fall. [The Curtis](https://www.thecurtis.com/) downtown has 13 themed floors and Hyper-Themed Rooms inspired by arcade games, pop culture and summer camp. The hotel's Corner Office Restaurant + Martini Bar is an easy first round, and the city's sports venues and bars are all within reach for a guys night out. ## Bend, Oregon - A Brewery Town With A Golf Course Bend is a brewery town that gets noticeably calmer after summer, and [Tetherow](https://tetherow.com/), a 700-acre resort on the edge of Deschutes National Forest, pairs a David McLay Kidd golf course with The Row, a pub pouring more than 30 beers with games on TV. Spend a day mountain biking, hiking, or fly fishing, then work through Bend's breweries in the evening. Fall adds beer festivals, harvest events and cooler weather for the golf course. ## Asheville, North Carolina - Breweries And The Blue Ridge Parkway Asheville built its reputation on beer, and the South Slope district downtown lets you walk between taprooms. Sierra Nevada's East Coast brewery is about 20 minutes south in Mills River. Fall color usually peaks along the Blue Ridge Parkway in mid to late October. Check the road status before you plan a drive, since some sections of the Parkway have had long closures for repairs. ## Grand Rapids, Michigan - Beer City USA I did a Grand Rapids beercation with a group of guys in the middle of winter, with a Brewsader passport to fill, and we hit 11 breweries between us, from Founders Brewing and Brewery Vivant to The Mitten Brewing Company. When the weather cooperates, many of them are within walking distance of downtown. The city is a few hours' drive from Chicago, Detroit and Indianapolis, so it's a long weekend within reach of most of the Midwest. Here's the full rundown of our [Grand Rapids beercation](blog/grand-rapids-beercation.html). ## Walla Walla, Washington - More Than 100 Wineries Around A Small Downtown Walla Walla, in southeastern Washington, has well over 100 wineries, and dozens of tasting rooms sit right downtown, so a couple can park the car for the weekend. Harvest runs through September and October, and the valley's red wines, especially cabernet and syrah, are the reason to go. It's a small town, so book dinner reservations early on fall weekends. ## St. Joseph, Michigan - Lake Michigan Shore Wine Country St. Joseph sits on a bluff above Lake Michigan, about 90 miles from Chicago and the wineries of the Lake Michigan Shore wine region are a short drive from the beach. Round Barn in Baroda makes wine, beer and spirits in one place, which settles the beer-or-wine argument, and Silver Beach is right below downtown for a walk at sunset. Don't miss the chance to explore the area's you-pick apples, fresh made pies, and craft beer as well. Southwest Michigan has a wide variety of other beach towns and agricultural areas to explore as well and the fall colors are always amazing this time of year! ## How To Plan A Tasting Weekend That Works For Everyone Each of these places works as a guys night or a couple's weekend, and the right pick depends on who's in the car. ### Match The Trip To Who's Coming A newly married couple wants a place like the Willamette Valley or Walla Walla, where the pace is slow and the B&B is part of the trip. A guys night wants density: Grand Rapids, Denver and Asheville put several taprooms within walking distance of each other. ### Book The One Thing That Sells Out Most of these trips have one reservation that fills first. In Frankfort it's the Buffalo Trace tour, which books up months in advance, and small-group outings like the e-bike ride in Charlottesville only have so many seats. Book that before you book flights, then build the rest around it. ### Mix In Something That Isn't A Tasting A canoe on the Kentucky River, the Walkway Over the Hudson or a hike at Silver Falls gives everyone a clear head for the afternoon pours. ### Join The Wine Club Only If You'll Drink It Tasting rooms are good at selling memberships, and most waive a fee or two for signing up. Before you commit, add up the shipments for a year and ask whether you'll finish them, because on an early-career budget, three cases of cabernet can crowd out next year's trip. Top Picks Flow Voyages ### Book your next cruise with Heather at Flow Voyages Flow Voyages is a travel advisor specializing in cruises and resorts. [Contact Flow Voyages](https://ads.flowmediamarketing.com/go/LdmfukWT7JJf2k7updeRkQ.617) Promoted by FlowAds **Hey James Hills wants you to share this!**   --- [Follow me on Facebook (opens in new window)](https://facebook.com/mantripping)[Follow me on X (opens in new window)](https://twitter.com/mantripping)[Follow me on Instagram (opens in new window)](https://instagram.com/mantripping)[Follow me on LinkedIn (opens in new window)](https://www.linkedin.com/in/jameshills2/)[PLG_FIELDS_OCHFOLLOWME_ARIA_NOTSUPPORTED](https://www.mantripping.com)   Written by: [James Hills](https://menwhoblog.com/james-hills.html) #MenWhoBlog MemberBlog MasterThought Leader James' passion for exploration and sense of duty to his community extends beyond himself. This means he is dedicated to providing a positive role model for other men and especially younger guys that need support so that they can thrive and be future positive contributors to society. 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