Top 5 Weekend Motorcycle Trips from Boston

Boston may be steeped in colonial cobblestone and revolutionary lore, but it’s also a launchpad to some of the finest weekend motorcycle escapes in the Northeast. Whether you're carving twisties through the White Mountains, coasting up to Portland for lobster rolls, or chasing Olympic memories in Lake Placid, these five routes will recharge your spirit, sharpen your skills, and deliver the kind of freedom only found behind handlebars.

Below are five curated weekend rides from Boston—each thoughtfully planned with scenic routes, great meals, comfortable stays, and that unmistakable joy of the open road.

1. Lake Placid, NY: A High Peaks Adventure

Total: 560 miles roundtrip

Best for: Twisty Adirondack roads, Olympic history, and mountain views

Start with breakfast at The Friendly Toast, then head west on Route 2 toward the Berkshires, climbing through Greenfield and North Adams before dipping into Vermont and riding through Keene, NY. Lunch at The People’s Pint sets the tone for local flavor, but the real highlight comes as you twist into the Adirondack Park. You'll roll into Lake Placid with enough time to explore the Olympic sites, then settle in at The Golden Arrow Lakeside Resort after dinner and drinks at Lake Placid Pub & Brewery.

Destination Focus:

Lake Placid is more than a mountain town—it's a historical gem, a two-time Olympic host, and a peaceful lakeside retreat. Visit the ski jumps or stroll Mirror Lake at sunset. This is a destination that rewards effort with elevation and soul-soothing stillness.

2. White Mountains & Kancamagus Highway, NH: New England’s Crown Jewel

Total: 300 miles roundtrip

Best for: Sweeping mountain curves, historical stops, forest photography

Begin your ride at The Friendly Toast, then carve north toward Canterbury Shaker Village, where serene backroads and preserved history collide. After refueling at Polly’s Pancake Parlor, the real thrill begins on the legendary Kancamagus Highway. You'll ride beneath the canopy of the White Mountains and rest at Indian Head Resort. Dinner at The Common Man rounds out the evening.

Day two includes breakfast at Flapjacks, then a meandering ride through Franconia Notch State Park. Visit waterfalls, photograph The Basin, and grab a bite at Woodstock Inn Brewery before the smooth cruise back to Boston.

Destination Focus:

The White Mountains offer the kind of motorcycling magic riders dream of—steep climbs, forested descents, and endless corners to chase. The Kancamagus is a must-ride: a corridor of beauty and technical satisfaction.

3. Portland & Coastal Maine: Lobster Rolls and Lighthouse Vistas

Total: 240 miles roundtrip

Best for: Seaside culture, Route 1A views, and fresh seafood

Your weekend begins at Flour Bakery + Cafe in Boston before taking the long, coastal way via Route 1A through Revere, Lynn, Salem, and Hampton, NH. Stop in Portsmouth to explore Strawbery Banke Museum, then grab lunch at The Friendly Toast. You'll continue through York to Cape Neddick for a look at Nubble Lighthouse, before arriving in Portland. Dinner at Eventide Oyster Co. and a stay at The Press Hotel complete the day.

The return trip hits Old Orchard Beach and The Lobster Shack at Two Lights, winding through classic seaside towns like Kennebunk, Portsmouth, and Newburyport.

Destination Focus:

Portland offers the perfect blend of maritime grit and culinary charm. Cobblestone streets lead to creative restaurants, old ports, and thriving craft breweries. It’s coastal New England, distilled and delicious.

4. Litchfield, CT: Rolling Hills and Colonial Charm

Total: 300 miles roundtrip

Best for: Relaxed riding, conservation trails, and historic New England

Fuel up at Trident Booksellers & Cafe before cruising west via Route 20 through Sudbury, Harvard, and Concord. Lunch is a farm-to-table affair at Arethusa al tavolo in Bantam. Afterward, explore 4,000 acres of preserved land at White Memorial Conservation Center, and wind down at The Litchfield Inn following dinner at @ The Corner.

On day two, breakfast at Patty’s Restaurant sets the tone for a scenic return via Route 202. Along the way, stop at Walden Pond and have lunch at Gibbet Hill Grill in Groton before closing out with seafood at Legal Sea Foods in Boston.

Destination Focus:

Litchfield County is a rider’s New England postcard—rolling hills, colonial homes, and stone walls flanking shaded lanes. It’s more serene than rugged, but every bit as rewarding.

5. Mystic, CT: Coastal Roads and Maritime Lore

Total: 300 miles roundtrip

Best for: Maritime history, casual waterside dining, and classic New England towns

Ride US-1 from Boston through Dedham and Norwood, aiming for a mid-morning stop at the Rhode Island State House. Lunch at Julian’s in Providence hits the spot before a scenic ride on CT-138 lands you in Mystic. Here, Mystic Seaport Museum, Red 36, and a night at The Whaler’s Inn complete a perfect coastal day.

The next morning begins with pastries at Sift Bake Shop, followed by a ride through Stonington Borough and a visit to Stonington Lighthouse Museum. Grab lunch at Dog Watch Café, then cruise back along MA-3A for a final dinner at Union Oyster House in Boston.

Destination Focus:

Mystic blends salty sea air with historic texture. From 19th-century whaling ships to waterfront dining, this ride is a love letter to New England’s maritime soul.

Try these trips or create your own at https://throttlemap.ai/plan