# Harvest Season Guys Trips To Wine Country, From Sonoma To The Hudson Valley *By James Hills — Updated October 2026* Fall is harvest season in American wine country, and it makes a strong guys trip when the tasting rooms come paired with hiking, golf, breweries and a football game. These ten wine regions run from Sonoma, the Mendocino Coast and the Central Coast to Oregon's Willamette and Tualatin Valleys, the Hudson Valley, Charlottesville and Southwest Michigan, each with enough to do for the guys who would rather drink beer. **Questions****Planning A Wine Trip For A Group That Is Not All Wine Guys****Article Index** ** No answer selected. Please try again. Please select either existing option or enter your own, however not both. Please select minimum {0} answer(s). Please select maximum {0} answer(s). /polls/travel-and-trip-ideas/what-do-you-prefer-to-call-your-guys-trips.html?task=poll.vote&format=json 1 Guys Trips (568 votes / 44.2%) 44.2% votes Guys Getaways (130 votes / 10.12%) 10.12% votes Mancations (118 votes / 9.18%) 9.18% votes Brocations (167 votes / 13%) 13% votes [{"id":5,"title":"Guys Weekends","votes":302,"type":"x","order":1,"pct":23.5,"resources":[]},{"id":6,"title":"Guys Trips","votes":568,"type":"x","order":2,"pct":44.2000000000000028421709430404007434844970703125,"resources":[]},{"id":7,"title":"Guys Getaways","votes":130,"type":"x","order":3,"pct":10.1199999999999992184029906638897955417633056640625,"resources":[]},{"id":8,"title":"Mancations","votes":118,"type":"x","order":4,"pct":9.17999999999999971578290569595992565155029296875,"resources":[]},{"id":9,"title":"Brocations","votes":167,"type":"x","order":5,"pct":13,"resources":[]}] ["#ff5b00","#4ac0f2","#b80028","#eef66c","#60bb22","#b96a9a","#62c2cc"] ["rgba(255,91,0,0.7)","rgba(74,192,242,0.7)","rgba(184,0,40,0.7)","rgba(238,246,108,0.7)","rgba(96,187,34,0.7)","rgba(185,106,154,0.7)","rgba(98,194,204,0.7)"] 350 ** Vote Now** Vote Form** ResultVotes Most groups have one guy who knows his tannins and three who want a cold beer, so plan a wine weekend that works for both. - **Hire a driver or book a tour -** tasting rooms are spread across the countryside, and an e-bike tour, a guide or a designated driver keeps the whole group tasting. - **Cap it at two or three wineries a day -** a long lunch and a brewery stop between tastings keep the day from turning into a blur. - **Mix in the breweries and distilleries -** every region on this list has craft beer, cider or spirits within a short drive of the vineyards. - **Agree on a bottle budget before the first tasting -** decide how many bottles each guy is bringing home, so the trunk and the credit cards both survive the weekend. - **Bring a rain jacket to the Pacific Northwest and the North Coast -** fall weather in Oregon and on the Mendocino Coast can turn wet quickly. 1. [Sonoma County, California - Redwoods, Russian River Beer And Harvest](https://www.mantripping.com/travel/wine-harvest-fall-guys-trips.html#sonoma-county,-california---redwoods,-russian-river-beer-and-harvest) 2. [The Mendocino Coast, California - Whiskey Flights, Whales And A Quiet Coast](https://www.mantripping.com/travel/wine-harvest-fall-guys-trips.html#the-mendocino-coast,-california---whiskey-flights,-whales-and-a-quiet-coast) 3. [Cambria And Paso Robles, California - Harvest Month On Highway 1](https://www.mantripping.com/travel/wine-harvest-fall-guys-trips.html#cambria-and-paso-robles,-california---harvest-month-on-highway-1) 4. [Pismo Beach, California - A Beach Base For Central Coast Wine Country](https://www.mantripping.com/travel/wine-harvest-fall-guys-trips.html#pismo-beach,-california---a-beach-base-for-central-coast-wine-country) 5. [Santa Barbara And The Santa Ynez Valley, California - Vintners Weekend And The Funk Zone](https://www.mantripping.com/travel/wine-harvest-fall-guys-trips.html#santa-barbara-and-the-santa-ynez-valley,-california---vintners-weekend-and-the-funk-zone) 6. [Tualatin Valley, Oregon - Wine, Sake And Trails West Of Portland](https://www.mantripping.com/travel/wine-harvest-fall-guys-trips.html#tualatin-valley,-oregon---wine,-sake-and-trails-west-of-portland) 7. [Willamette Valley, Oregon - Tasting With The Winemaker](https://www.mantripping.com/travel/wine-harvest-fall-guys-trips.html#willamette-valley,-oregon---tasting-with-the-winemaker) 8. [Hudson Valley, New York - The Shawangunk Wine Trail And Sunday Football](https://www.mantripping.com/travel/wine-harvest-fall-guys-trips.html#hudson-valley,-new-york---the-shawangunk-wine-trail-and-sunday-football) 9. [Charlottesville, Virginia - E-Bike Wine Tours, Polo And UVA Football](https://www.mantripping.com/travel/wine-harvest-fall-guys-trips.html#charlottesville,-virginia---e-bike-wine-tours,-polo-and-uva-football) 10. [St. Joseph And Southwest Michigan - Lake Michigan Shore Wine Country](https://www.mantripping.com/travel/wine-harvest-fall-guys-trips.html#st.-joseph-and-southwest-michigan---lake-michigan-shore-wine-country) 11. [West Coast, East Coast Or The Midwest: Picking A Harvest Weekend](https://www.mantripping.com/travel/wine-harvest-fall-guys-trips.html#west-coast,-east-coast-or-the-midwest:-picking-a-harvest-weekend)[Let Travel Time Decide The Coast](https://www.mantripping.com/travel/wine-harvest-fall-guys-trips.html#let-travel-time-decide-the-coast) 12. [Pick The Region With The Best Non-Wine Day](https://www.mantripping.com/travel/wine-harvest-fall-guys-trips.html#pick-the-region-with-the-best-non-wine-day) 13. [Choose Between Harvest Weather And Empty Tasting Rooms](https://www.mantripping.com/travel/wine-harvest-fall-guys-trips.html#choose-between-harvest-weather-and-empty-tasting-rooms) Nearly every region here built its pitch around a harvest-season weekend for a group of guys. ## Sonoma County, California - Redwoods, Russian River Beer And Harvest [Sonoma County](https://www.sonomacounty.com/) combines more than 50 miles of Pacific coastline, redwood forests and the Russian River with wine harvest in the fall. Hike or swim at Lake Sonoma, walk Armstrong Redwoods State Natural Reserve, play Bennett Valley Golf Course, then taste at St. Francis Winery in the Valley of the Moon, Rodney Strong in Alexander Valley or Benziger Family Winery. The beer drinkers get Russian River Brewing Company, and nights can run to Graton Resort & Casino, which books nationally known comedians and musicians. Stay at the Fairmont Sonoma Mission Inn & Spa for golf and pools, the Flamingo Resort & Spa in Santa Rosa near the breweries, or The Lodge at Bodega Bay for the coast. ### How to Plan a Vegas Bachelor Party (and not piss off the bride) Tips and advice on how to plan the perfect Las Vegas Bachelor Party, without pissing off the bride to be. ManTripping [Read More](https://ads.flowmediamarketing.com/go/S-oXNQQ0XSssSJvwCOzgOQ.1043) ### Egypt's Red Sea Resorts: Dive, Golf, and Desert Thrills for a Guys Trip Men's guide to Egypt beach resorts: Red Sea adventures, luxury all-inclusive stays, and desert excursions. Experience championship golf and nightlife in Sharm El Sheikh. Perfect for groups seeking adventure and relaxation. ManTripping [Read More](https://ads.flowmediamarketing.com/go/S-oXNQQ0XSssSJvwCOzgOQ.1483) ### 8 Days in Mallorca Classic Discover the Balearic Islands at your own pace. Sea or mountain, culture or beach, quite coves or crowded clubs, it´s all here in the beautiful Mallorca. Your stay will be splitted in two different hubs so you'll be able to make the most of it. Viator (affiliate) [See Current Price](https://ads.flowmediamarketing.com/go/S-oXNQQ0XSssSJvwCOzgOQ.1305) ### Majesty Of Untouched Northern Vietnam Tour 6 Days A 6-day northern Vietnam tour through Ha Giang, Ba Be Lake and Ban Gioc Waterfall, ideal for nature lovers seeking untouched landscapes. Viator (affiliate) [See Current Price](https://ads.flowmediamarketing.com/go/S-oXNQQ0XSssSJvwCOzgOQ.558) Promoted by FlowAds ## The Mendocino Coast, California - Whiskey Flights, Whales And A Quiet Coast The Mendocino Coast, about three and a half hours from San Francisco, slows down in the fall, with warm days, crisp nights, migrating whales visible from shore and local mushrooms on every menu once the rain starts. Nearby Anderson Valley adds a quieter California wine region to the weekend. In Fort Bragg, [Noyo Harbor Inn](http://noyoharborinn.com/) pours whiskey flights from about 100 whiskeys at its HarborView Bistro & Bar and has a cigar lounge in an outdoor gazebo with a fire pit. Little River Inn has ocean views from every room, the only golf course on this stretch of coast and Ole's Whale Watch Bar, where locals still tell the story of James Dean getting kicked out. Stanford Inn by the Sea lends free bikes and rents canoes and outriggers for the Big River Estuary. ## Cambria And Paso Robles, California - Harvest Month On Highway 1 [Cambria](https://visitcambriaca.com/), on Highway 1 in San Luis Obispo County, is a base for two October traditions: Paso Robles Harvest Wine Month about 30 minutes inland, and Cambria's month-long Scarecrow Festival with more than 200 scarecrows around town. Mid-October is usually the strongest window for harvest events. ## Man Gear Pick of the Month September's Pick Amazon (affiliate) ### Kenyon City Grill Portable Stainless Steel Electric Grill Why we picked it: a grill you can actually carry to the campsite, the tailgate or the cabin without borrowing a truck. Stainless, no propane tank to wrestle, and hot enough to cook for four guys rather than reheat for one. [Check The Price](https://ads.flowmediamarketing.com/go/j3QQfhaKhKMYo236dLmmcA.2144) [August's Pick LiberNovo Maxis Electric Big and Tall Ergonomic Office Chair, Graphite 52cm $1,466.00](https://ads.flowmediamarketing.com/go/j3QQfhaKhKMYo236dLmmcA.2350) [July's Pick Powerful Propane Torch Gun, Adjustable Flame Thrower Gun, Kitchen Torch with Detachable Design, Flamethrower Blow Torch for BBQ, Searing Steak, Welding, Camping Charcoal Lighter(Tank Not Included) $41.99](https://ads.flowmediamarketing.com/go/j3QQfhaKhKMYo236dLmmcA.2397) [June's Pick OYASUMI Funny BBQ Man Hot Dog Holders, 4 PCS Reusable Stainless Steel Sausage Stands, Portable Hot Dog Roasters, Barbecue Grill Accessories for Camping & Party Gifts $14.98](https://ads.flowmediamarketing.com/go/j3QQfhaKhKMYo236dLmmcA.2396) Promoted by FlowAds Spend day one kayaking or rock fishing off Moonstone Beach or hiking the blufftop trails of the 437-acre Fiscalini Ranch Preserve. Day two is Paso Robles, mixing wineries with breweries, distilleries and barbecue. Day three heads north on Highway 1 to Hearst Castle and the elephant seals at Piedras Blancas. Oceanpoint Ranch on Moonstone Beach Drive has fire pits, a modern cowboy look and brisket hash for breakfast at The Cow Tipper. ## Pismo Beach, California - A Beach Base For Central Coast Wine Country Pismo Beach, about halfway between Los Angeles and San Francisco, gives the group a beach base with Central Coast wine country in day-trip range: the Edna Valley outside San Luis Obispo, Paso Robles to the north and the Santa Maria Valley to the south. Spend one day on the water, with a lesson from Sandbar Surf School and clam chowder in a sourdough bread bowl at Splash Cafe, and another riding ATVs or side-by-sides on the Oceano Dunes. Back in town, The Deck at [Sandcastle Hotel on the Beach](https://www.sandcastlehotelonthebeach.com/) handles sunset beers over the Pacific, with bucket-style seafood at Cracked Crab and oysters and steaks at The Oyster Loft. October usually brings the Surfing for Hope Longboard Classic at the pier and, in mid-October, the Pismo Beach Clam Festival with its Clam Chowder Cook-Off. ## Santa Barbara And The Santa Ynez Valley, California - Vintners Weekend And The Funk Zone [Santa Barbara](https://santabarbaraca.com/) in October is shoulder season, with weather in the 70s and rates below summer. Mid-October usually brings the Santa Barbara Vintners Festival at the Firestone Estate in the Santa Ynez Valley, pouring from Santa Barbara County wineries, and the Santa Barbara Harbor & Seafood Festival, celebrating local lobster season, often on the same weekend. Back in town, walk the Urban Wine Trail through the Funk Zone to Santa Barbara Winery, Paradise Springs Winery, Margerum & Barden Wines and Fox Wine Co. & Blair Fox Cellars. Burn off the night before on Inspiration Point, a 3.4-mile out-and-back with nearly 1,000 feet of climbing, book a half day for rockfish and lobster with Santa Barbara Sport Fishing Charters, or play Sandpiper Golf Club or Glen Annie Golf Club, both open to the public. Figueroa Mountain Brewing and Institution Ale show the games, and The Lark and Lucky Penny handle dinner. ## Tualatin Valley, Oregon - Wine, Sake And Trails West Of Portland [Tualatin Valley](https://tualatinvalley.org/), 30 to 45 minutes from Portland International Airport, is the closest wine country to Portland, with more than 40 wineries and tasting rooms and about two dozen breweries. Late September to mid-October is the peak for fall color, with moderate temperatures. Kayak the slow-moving Tualatin River National Water Trail with rentals from Alder Creek, ride the 21-mile Banks-Vernonia State Trail across its 80-foot trestle, or take the Pumpkin Ridge Zip Tour, which runs weekends into mid-October. Taste at Dauntless Wine Co., which is veteran-owned, or David Hill Vineyards & Winery, and learn how sake is made at SakeOne, Oregon's only sake brewery. McMenamins Grand Lodge adds a soaking pool and a movie theater, and the Cedartree Hotel has a sake bar and onsen-style pools. ## Willamette Valley, Oregon - Tasting With The Winemaker The Willamette Valley has more than 700 wineries, and many are small enough that the group ends up tasting with the owner or the winemaker, at places like JL Kiff Vineyard, Compris Vineyard and Bells Up Winery. September has the driest weather, October is good too, and by November the crowds thin out. At Beckham Estate, the winemaker makes his own clay amphorae for aging wine. Between tastings, hike Silver Falls State Park, play Chehalem Glenn Golf Course, which is built on sand and drains fast after fall rain, or book a hot air balloon ride over Newberg. [Chehalem Ridge Bed & Breakfast](http://www.chehalemridge.com/) sits 1,000 feet up Chehalem Mountain with five rooms and a chef-innkeeper who cooks a three-course breakfast. ## Hudson Valley, New York - The Shawangunk Wine Trail And Sunday Football The Hudson Valley wine country between Poughkeepsie and New Paltz sits about 90 minutes north of New York City, with wineries, distilleries, hiking and football Sundays all within a 30-minute drive of [The Heartwood at Vassar](https://theheartwood.com/). Fall adds grape-stomping and harvest festivals at the wineries, plus the New York State Sheep and Wool Festival and the Rosendale International Pickle Festival in mid-October. Walk the Walkway Over the Hudson, billed as the tallest and longest pedestrian walkway, for river views and changing leaves, then taste along the 13-winery Shawangunk Wine Trail at Robibero Winery, Benmarl Winery and Quartz Rock Vineyard and Cider House. Save Sunday for brunch and a distillery tour at The Hudson House Distillery, pizza at Mill House Brewing and football on the rooftop at Zeus Brewing Company. ## Charlottesville, Virginia - E-Bike Wine Tours, Polo And UVA Football Charlottesville lies at the foot of the Blue Ridge Mountains, and September through early November brings grape harvest along the Route 151 wine trail, peak color and UVA home football. [Shifting Gears Travel](https://www.sgtrips.com) runs e-bike tours with a sommelier guide through two wineries, with vineyard walks and lunch. Play a round at the Boar's Head Inn, float the James River with the James River Batteau Company on the kind of river boat Virginians used 200 years ago, and eat beef-tallow fries at the Red Rose Pub before kickoff. [Virginia Guesthouse Hotel](https://www.virginiaguesthouse.com/) sits on the UVA Grounds, with the rooftop bar The Perch for drafts and mountain views, and Sunday polo at King Family Vineyards and hikes in Shenandoah fill the last day. ## St. Joseph And Southwest Michigan - Lake Michigan Shore Wine Country Lakefront bluffs frame St. Joseph, on Lake Michigan about 90 minutes from Chicago, and the tasting rooms, cideries and breweries of the Lake Michigan Shore wine region are a short drive inland, with fall color and the harvest arriving together. It makes an easy harvest weekend for Midwest groups that want wine without a flight, and our [Southwest Michigan guys trip ideas](https://www.mantripping.com/united-states/michigan/southwest-michigan.html) cover where to stay and eat. ## West Coast, East Coast Or The Midwest: Picking A Harvest Weekend The list runs from the Pacific coast to the East, with one stop in the Midwest, and the right pick depends on travel time and how much wine the group wants. ### Let Travel Time Decide The Coast West Coast groups can drive to Sonoma, Mendocino, the Central Coast or Oregon. East Coast groups have the Hudson Valley 90 minutes from New York City and Charlottesville in the Blue Ridge, and Midwest groups can reach Southwest Michigan from Chicago. ### Pick The Region With The Best Non-Wine Day The trips that work best for mixed groups pair wine with something else: a UVA game in Charlottesville, whiskey and cigars on the Mendocino Coast, the Banks-Vernonia trail in Tualatin Valley, the Oceano Dunes near Pismo Beach or Sunday football on a rooftop in the Hudson Valley. ### Choose Between Harvest Weather And Empty Tasting Rooms September and early October bring the best weather and the harvest festivals, while November brings more rain but emptier tasting rooms, and in the Willamette Valley more time with the people who make the wine. ### 5 Ways To Have the Ultimate Detroit Guys Weekend ManTripping: Men's Travel and Lifestyle Blog for busy men who love to travel. ManTripping [Read More](https://ads.flowmediamarketing.com/go/MilC2YF6UMCzYgTY9SALUg.348) ### Why You Should Consider Michigan For Your Next Guys Weekend Getaway Michigan guys weekend getaway ManTripping [Read More](https://ads.flowmediamarketing.com/go/MilC2YF6UMCzYgTY9SALUg.344) ### How to Finance Your Guys Cruise Trip Without Breaking the Bank Discover smart ways to finance your next guys cruise trip without breaking the bank. From sinking funds to payment plans with Uplift and Virgin Voyages, learn how to maximize your budget for epic adve ManTripping [Read More](https://ads.flowmediamarketing.com/go/MilC2YF6UMCzYgTY9SALUg.426) Promoted by FlowAds 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/x3K_qE1G-LNOKfwTrBcdEw.617) Promoted by FlowAds Details Written by: James Hills Last Updated: 02 October 2026 ### 🚢Ready To Book A Vacation? Let us help you plan a cruise, all-inclusive resort, or tour for your next guys trip, family vacation, or romantic getaway. Click here to [**Book Your Next Vacation**](https://www.mantripping.com/vacation-planning.html). #### Which Style Of Amazon Cruise Should You Pick To Explore World's Largest River? Aug 17, 2026 [Which Style Of Amazon Cruise Should You Pick To Explore World's Largest River?](https://www.mantripping.com/travel/amazon-river-cruise-planning-ship-options.html) [Plan Your Next Vacation Today!](https://www.mantripping.com/vacation-planning.html) ### Products & Gift Ideas #### LiberNovo Maxis Chair Review - Finally A Seat That Lets Big Dudes Feel Comfortable At The Desk Sep 10, 2026 [LiberNovo Maxis Chair Review - Finally A Seat That Lets Big Dudes Feel Comfortable At The Desk](https://www.mantripping.com/stuff/libernovo-maxis-big-and-tall-office-chair-review.html) #### FRESKO 4-in-1 Immersion Hand Blender Review Sep 09, 2026 [FRESKO 4-in-1 Immersion Hand Blender Review](https://www.mantripping.com/stuff/fresko-4-in-1-immersion-hand-blender-review.html) #### UGREEN Air Review: Four Slim Chargers And Power Banks I Traveled With This Summer Aug 25, 2026 [UGREEN Air Review: Four Slim Chargers And Power Banks I Traveled With This Summer](https://www.mantripping.com/stuff/ugreen-air-chargers-power-banks-review.html) ### Top Guys Trip Ideas: #### New Zealand's Adrenaline Capital: Epic Auckland Adventures for Thrill-Seeking Groups Of Guys Aug 10, 2025 [New Zealand's Adrenaline Capital: Epic Auckland Adventures for Thrill-Seeking Groups Of Guys](https://www.mantripping.com/travel/auckland-guys-trip-ideas-for-adventure-seekers.html) #### Cruises Are Expensive, Here's How to Finance Your Guys Trip Without Sinking Your Wallet Jun 20, 2026 [Cruises Are Expensive, Here's How to Finance Your Guys Trip Without Sinking Your Wallet](https://www.mantripping.com/travel/financing-guys-cruise-vacation-guide.html) #### Awesome Port Cities for a Mancation Cruise That Aren't In Florida Oct 17, 2017 [Awesome Port Cities for a Mancation Cruise That Aren't In Florida](https://www.mantripping.com/travel/awesome-port-cities-for-a-mancation-cruise-that-aren-t-in-florida.html) ### Related Articles #### How To Commemorate A Guys Trip With A Custom Challenge Coin [How To Commemorate A Guys Trip With A Custom Challenge Coin](https://www.mantripping.com/stuff/custom-challenge-coin-guys-trip.html) #### More Than Caribbean Beaches, Eight All-Inclusive Resorts Built for The Perfect Father-Son Getaway [More Than Caribbean Beaches, Eight All-Inclusive Resorts Built for The Perfect Father-Son Getaway](https://www.mantripping.com/travel/all-inclusive-resorts-father-son-getaway.html) #### What Makes Las Vegas Still the Best Guys Trip Destination? [What Makes Las Vegas Still the Best Guys Trip Destination?](https://www.mantripping.com/travel/different-styles-las-vegas-guys-trips.html) #### Our Picks For 28 of the Best Resorts for a Father-Son Getaway [Our Picks For 28 of the Best Resorts for a Father-Son Getaway](https://www.mantripping.com/travel/best-resorts-father-son-getaway.html) #### 10 Things That Changed in Las Vegas Since Your Last Guys Trip - Updated 2026 [10 Things That Changed in Las Vegas Since Your Last Guys Trip - Updated 2026](https://www.mantripping.com/travel/whats-new-las-vegas-guys-trip.html) - [**](https://www.mantripping.com/search.html) - [**](https://www.mantripping.com/sitemap.html) - [** Polls](https://www.mantripping.com/polls.html) - [Community Login](https://www.mantripping.com/registration/login.html) - [Brand Engagement Newsletter](https://www.mantripping.com/pr-ops-newsletter.html) - [Links](https://www.mantripping.com/links.html) - [Pitch Portal](https://www.mantripping.com/pitch.html) - [Men's Travel Survey](https://www.mantripping.com/the-mantripping-guys-trip-report-spring-2026.html) --- *Source: [Harvest Season Guys Trips To Wine Country, From Sonoma To The Hudson Valley](https://mantripping.com/travel/wine-harvest-fall-guys-trips.html)* **Tags:** New York State Guys Trip Ideas, California Guys Trip Ideas, Michigan Guys Trip Ideas, Oregon Guys Trip Ideas, Virginia Guys Trip Ideas, Travel Ideas, Guys Trip