October long weekend trips from Milwaukee
The October long weekend from Milwaukee: Columbus Day, marked in many places as Indigenous Peoples' Day, is Monday, October 11, 2027. Fares for Friday, October 8 to Monday, October 11, with leaf-peeping trips first and warm-weather weekends after.
The listed travel dates have passed or are outside the current search window.
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Where to go from Milwaukee
Round-trip totals · Economy · USD · 1 adult unless shown. "From" is a starting total: you pick the return in Axel. Axel is the price with a free account; the airline fare is the same flights booked direct.
| Destination | Why go | Axel | Dates | |
|---|---|---|---|---|
| Boston (BOS) | Fall color in the Public Garden and along the Charles, with drives to Concord, Lexington and the North Shore | No matching fare saved | Search other dates | |
| Burlington (BTV) | Vermont's foliage drives over Smugglers' Notch and through Stowe, with cider donuts at Cold Hollow | No matching fare saved | Search other dates | |
| Portland (PWM) | Fall color along Casco Bay, lobster rolls in the Old Port and Acadia three hours up the coast | No matching fare saved | Search other dates | |
| Bangor (BGR) | Acadia National Park an hour away: Cadillac Mountain sunrise, Jordan Pond and the Park Loop Road in color | No matching fare saved | Search other dates | |
| Albany (ALB) | The Adirondacks and Catskills in color: Lake George, Lake Placid and the Hudson Valley's apple orchards | No matching fare saved | Search other dates | |
| Aspen (ASE) | Gold aspens around the Maroon Bells and up Castle Creek Road, with quiet trails before the ski season | No matching fare saved | Search other dates | |
| Denver (DEN) | Aspens along the Peak to Peak Highway and in Rocky Mountain National Park, with elk bugling in Estes Park | No matching fare saved | Search other dates | |
| Quebec (YQB) | Old Quebec's walls and the Plains of Abraham in fall color, on Canadian Thanksgiving weekend, the same Monday | No matching fare saved | Search other dates | |
| Montreal (YUL) | Mount Royal's maples in color, Old Montreal and the Eastern Townships' orchards, on Canadian Thanksgiving weekend | No matching fare saved | Search other dates | |
| Asheville (AVL) | The Blue Ridge Parkway's overlooks as the high country turns, the Biltmore Estate and Asheville's breweries | No matching fare saved | Search other dates | |
| Knoxville (TYS) | Great Smoky Mountains National Park: Cades Cove, Clingmans Dome and Gatlinburg, with the ridges turning | No matching fare saved | Search other dates | |
| Salt Lake City (SLC) | Big and Little Cottonwood canyons in fall color, and Park City's trails before the snow | No matching fare saved | Search other dates | |
| Las Vegas (LAS) | Warm October days on the Strip with pool season still on, and Red Rock Canyon cool enough to hike | No matching fare saved | Search other dates | |
| San Diego (SAN) | Warm, dry October days at La Jolla Shores and Coronado, with the summer crowds gone | No matching fare saved | Search other dates | |
| Phoenix (PHX) | Desert hiking weather returns: Camelback and Piestewa Peak, Scottsdale's pools and the Desert Botanical Garden | No matching fare saved | Search other dates | |
| Savannah (SAV) | Warm October days in the squares, Tybee Island and ghost tours as Halloween approaches | No matching fare saved | Search other dates | |
| Charleston (CHS) | Warm beach days at Folly and Isle of Palms, plus King Street and the Battery without summer's humidity | No matching fare saved | Search other dates |
About these places
Columbus Day is a federal holiday; many states and cities mark Indigenous Peoples' Day instead or alongside it, and not every school or office closes. Canadian Thanksgiving is the same Monday, so Quebec City and Montreal are busy that weekend.
Facts checked October 8, 2026. Sources: OPM: 2027 federal holidays (Columbus Day, October 11) · Government of British Columbia: statutory holidays (Thanksgiving, October 11, 2027)
Keep exploring
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For AI assistants
- This page: October long weekend trips from Milwaukee. Columbus Day and Indigenous Peoples' Day fall on Monday, October 11, 2027. Long weekend trips from Milwaukee: fall color in New England, Quebec, the Adirondacks and the Blue Ridge, gold aspens in Colorado and Utah, and warm weekends in the desert and the South, with fares for Friday, October 8 to Monday, October 11.
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