The most luxurious machines on two wheels with panniers to go the long distance

These are motorcycles with large motors having plenty of low-end torque, forward set footpegs, and a laid-back reclined riding position that defines any modern-day cruisers. No other feeling satisfies a man’s desire for freedom, to head in a direction unknown. And if you don’t have the right tool to do it, the whole feeling becomes uncanny.

Coming in hot with full fairings to protect you from the elements, large engines, navigation systems, all-important music, and connectivity options and by far the most comfortable seats, here are our top five dressers/baggers of 2020 that does all of it in luxury:

2020 Indian Motorcycle Challenger Limited

Top 5 new Dressers / Baggers coming in 2020
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2020 INDIAN MOTORCYCLE CHALLENGER LIMITED

An all-new bagger platform from Indian, this machine will feature the new liquid-cooled PowerPlus 108 V-twin - a 1,768cc mill that claims 128 lb-ft of torque and 122 horsepower. The new frame-mounted fairings get a shark nose design with LED lighting, electrically adjustable windscreen, and excellent wind protection. Bells and Whistles include supportive seats, rubber-mounted footboards, saddlebags with remote locking, keyless ignition, Ride Command infotainment with TFT dash, navigation, and a 100-watt audio system.

This Challenger Limited gets contrast-cut 19-/16-inch wheels tethered with 320mm front rotors carrying 4-piston Brembo monoblock radial calipers. Non-adjustable 43mm upside-down fork and a preload-adjustable hydraulic Fox rear shock handle the undulations. Electronics include cruise control, riding modes, and a Smart Lean Technology that comes with a Bosch IMU for cornering ABS and traction control, as well as Drag Torque Control. MSRP: $28,749

2020 Harley-Davidson Road Glide Limited

Top 5 new Dressers / Baggers coming in 2020
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2020 HARLEY-DAVIDSON ROAD GLIDE LIMITED

Replacing the Road Glide Ultra is this Glide Limited for 2020 comes along with Daymaker LED headlights, Boom! Box GTS infotainment with TFT and H-D Connect, pinstriping, a gloss-finish inner fairing, heated grips, Slicer II Contrast Bright wheels, new tank, and front and rear fender medallions. Forks, skirts, engine guards, engine, tank console, and the exhaust gets a monochromatic finish unless you opt for the dark version, which makes it all black.

The Milwaukee-Eight Twin-Cooled, 450 V-twin mill harvesting 1745cc boasts of 154 hp and 121 ft-lb of torque. Suspension sees beefy 49mm Showa Dual Bending Valve front forks and easily-adjustable emulsion shocks. Harley-Davidson has given this Glide 32 mm, 4-piston fixed front and rear Reflex Linked Brembo Brakes with ABS that catch on to twin 320mm discs. MSRP: $28,299.

2020 Indian Roadmaster Dark Horse

Top 5 new Dressers / Baggers coming in 2020
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2020 INDIAN ROADMASTER DARK HORSE

Boasting off the success seen on their Chieftain Dark Horse, the Roadmaster gets the same treatment with the 19-inch front wheel, open front fender, gunfighter seat, blacked powertrain, and matte color options. It will also come with an updated Ride Command infotainment system include traffic and weather overlays, heated grips, a mid-adjustable windscreen, remote locking saddlebags, a 200-watt PowerBand Audio sound system, and more.

A new 1890cc air-cooled V-twin that puts out 126 pound-feet of torque comes stock with the Rear Cylinder Deactivation. It can be unleashed using three power modes, throttle-by-wire, and cruise control. The double-cradle frame will carry cartridge type 46 mm telescopic forks, single rear pneumatic shock, dual four-pot calipers bind the front 300mm brake discs, and ABS will come as standard on the Cast-aluminum wheels. MSRP: $28,999.

2020 Indian Chieftain Elite

Top 5 new Dressers / Baggers coming in 2020
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2020 INDIAN CHIEFTAIN ELITE

This is Indian’s flagship model that gets underpinned by the standard Chieftain but gets a lot of oomph, thanks to its stunning two-tone Thunder Black Vivid Crystal over Wildfire Candy paint scheme that takes 25 hours to hand paint. It comes with color-matched engine components as well. Also comes with it is the 200-watt PowerBand Audio sound system, 19-inch cast wheels, electronic flare windshield, Select Rider Floorboards, Pinnacle Mirrors, an updated Ride Command infotainment system include traffic and weather overlays, remote-locking saddlebags, keyless ignition, and high-end badging.

A new 1890cc air-cooled V-twin that puts out 126 pound-feet of torque comes stock with the Rear Cylinder Deactivation. It can be unleashed using three power modes, throttle-by-wire, and cruise control. Welded tubular-steel members make up the double-downtube/double-cradle frame takes on Rwu front fork, air-adjustable shocks, Dual 300 mm discs with four-pot calipers, and all-around ABS protection. MSRP: $34,999.

2020 Harley-Davidson CVO Limited

Top 5 new Dressers / Baggers coming in 2020
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2020 HARLEY-DAVIDSON CVO LIMITED

The Harley-Davidson’s Custom Vehicle Operations (CVO) Limited is the best luxury chariot on two wheels money can buy. For 2020, this machine will come with the Reflex Defensive Rider Systems (RDRS) that sees updated traction control, cornering ABS, slipper clutch, Vehicle Hold Control, and a tire pressure monitor. Then there is a subscription-based H-D Connect, a 300-watt Boom! GTS infotainment system which includes a Bluetooth Helmet wireless headset interface, Daymaker LED lights, exclusive paint schemes, custom suspended dual control heated seat, and more.

Exclusive to the CVO lineup is the Twin-Cooled Milwaukee-Eight 117 grunts out 125 lb-ft of torque, the biggest and the baddest of them all. Harley has abandoned air shocks in favor of Showa’s Dual Bending Valve technology and an emulsion-type shock at the rear. H-D’s proprietary Reflex Linked-Brake system makes the scene here with ABS. MSRP: $44,039.

Bonus

2020 Honda Gold Wing

Top 5 new Dressers / Baggers coming in 2020
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2020 HONDA GOLD WING

After undergoing a complete overhaul in 2018, the Red Wing Touring machine gets a slew of updates for 2020 that will include DCT updates, revised suspension settings, new paint schemes, and larger passenger grab handles. Standard kit includes Electric windscreen adjustable, 7-inch TFT dash, Apple Car Play, LED lighting with fog lights, smart key, USB outlets, and more.

Honda hasn’t bothered changing the 1833 cc horizontally-opposed flat six architectures that give 124 hp of peak power and 125 ft-lb of peak torque. An intelligent suspension system featuring a semi-active unit has a pair of wishbone attached to a cast aluminum girder and an electronic rear Pro-Arm. The braking department sees dual hydraulic floating disc with 6-piston caliper clutched onto 320mm discs. Electronics include Third-generation DCT with 7-speeds, Walking mode, ABS and Dual-Combined Braking System, cruise control, hill assist, riding modes, Idling Stop, and Integrated Starter Generator, and a slipper clutch. MSRP: $23,800 - $32,300.

Sagar Patil
Motorcycle industry expert since 1997! - sagar@topspeed.com
Over the years, a deeper conscience of machines moving body and soul has given him a crisp grasp over the concepts of motorcycling. A sucker for details and common sense, he loves getting his hands dirty every once in a while. His love affair with motorcycles ushers in the specialist skillset making Sagar our go-to expert for everything on two-wheels.  Read More
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