Trip length: 5–7 days; 424 miles (682km)
Best time to go: late September to mid-October
Essential photo: Kent Falls set against a backdrop of autumnal colors
Top experience: Zip lining through the tree canopy in Bretton Woods
The brilliance of fall in New England is legendary. Scarlet and sugar maples, ash, birch, beech, dogwood, tulip tree, oak and sassafras all contribute to the carnival of autumn color. But this trip is about much more than just flora and fauna: the harvest spirit makes for family outings to pick-your-own farms, leisurely walks along dappled trails, and tables that groan beneath delicious seasonal produce.
1. Lake Candlewood
With a surface area of 8.4 sq miles, Candlewood is the largest lake in Connecticut. On the western shore, the Squantz Pond State Park is popular with leaf-peepers, who come to amble the pretty shoreline. In Brookfield and Sherman, quiet vineyards with acres of gnarled grapevines line the hillsides. Visitors can tour the award-winning DiGrazia Vineyards (digrazia.com; 131 Tower Rd, Brookfield; 11am–5pm daily) or opt for something more intimate at White Silo Farm Winery (whitesilowinery.com; 32 CT 37; tastings $7; 11am–6pm Fri–Sun), where the focus is on specialty wines made from farm-grown fruit. For the ultimate bird’s eye view of the foliage, consider a late-afternoon hot-air-balloon ride with GONE Ballooning (flygoneballooning.com; 88 Sylvan Crest Dr; adult/under 12yr $250/125) in nearby Southbury.
From Danbury, at the southern tip of the lake, you have a choice of heading north via US 7, taking in Brookfield and New Milford (or trailing the scenic eastern shoreline along Candlewood Lake Rd S); or heading north along CT 37 and CT 39 via New Fairfield, Squantz Pond and Sherman, before reconnecting with US 7 to Kent.
Kent has previously been voted the spot in all of New England (yes, even beating Vermont) for fall foliage viewing. Situated prettily in the Litchfield Hills on the banks of the Housatonic River, it is surrounded by dense woodlands. For a sweeping view of them, hike up Cobble Mountain in Macedonia Brook State Park, a wooded oasis 2 miles north of town. The steep climb to the rocky ridge affords panoramic views of the foliage against a backdrop of the Taconic and Catskill mountain ranges.
The 2175-mile Georgiato-Maine Appalachian National Scenic Trail (appalachiantrail.org) also runs through Kent and up to Salisbury on the Massachusetts border. Unlike much of the trail, the Kent section offers a mostly flat 5-mile river walk alongside the Housatonic, the longest river walk along the entire length of the trail. The trailhead is accessed on River Rd, off CT 341.
The 15-mile drive from Kent to Housatonic Meadows State Park along US 7 is one of the most scenic drives in Connecticut. The single-lane road dips and weaves between thick forests, past Kent Falls State Park with its tumbling waterfall (visible from the road), and through West Cornwall’s picturesque covered bridge, which spans the Housatonic River.
3. Housatonic Meadows State Park
During the spring thaw, the churning waters of the Housatonic challenge kayakers and canoeists. By summer the scenic waterway transforms into a lazy, flat river perfect for fly-fishing. In the Housatonic Meadows State Park (806-672-6772; US 7; tent sites residents/nonresidents $17/27; mid-Apr–mid-Oct), campers vie for a spot on the banks of the river while hikers take to the hills on the Appalachian Trail. Housatonic River Outfitters (dryflies.com; 24 Kent Rd, Cornwall Bridge) runs guided fishing trips with gourmet picnics.
Popular with artists and photographers, one of the most photographed fall scenes is the Cornwall Bridge (West Cornwall), an antique covered bridge that stretches across the broad river, framed by vibrantly colored foliage. In the nearby town of Goshen is Nodine’s Smokehouse (nodinesmokehouse.com; 39 North St), a major supplier of smoked meats to New York gourmet food stores.
Continue north along US 7 toward the Massachusetts border and Great Barrington. After a few miles you leave the forested slopes of the park behind you and enter expansive rolling countryside dotted with large red-and-white barns. Look out for hand-painted signs advertising farm produce and consider stopping overnight in Falls Village, which has an excellent B&B.
Blanketing the westernmost part of Massachusetts, the rounded mountains of the Berkshires turn crimson and gold as early as mid-September. The effective capital of the Berkshires is Great Barrington, a formerly industrial town whose streets are now lined with art galleries and upscale restaurants. It’s the perfect place to pack your picnic or rest your legs before or after a hike in nearby Beartown State Forest. Crisscrossing some 12,000 acres, hiking trails yield spectacular views of wooded hillsides and pretty Benedict Pond, Further north, October Mountain State Forest is the state’s largest tract of green space (16,127 acres), also interwoven with hiking trails. The name – attributed to Herman Melville – gives a good indication of when this park is at its loveliest, with its multicolored tapestry of hemlocks, birches and oaks.
Drive north on US 7, the spine of the Berkshires, cruising through Great Barrington and Stockbridge. In Lee, the highway merges with scenic US 20, from where you can access October Mountain. Continue 16 miles north through Lenox and Pittsfield to Lanesborough. Turn right on N Main St and follow the signs to the park entrance.
5. Mt Greylock State Forest
Massachusetts’ highest peak is not so high, at 3491ft, but a climb up the 92ft-high War Veterans Memorial Tower rewards you with a forested panorama stretching up to 100 miles, across the Taconic, Housatonic and Catskill ranges, and over five states. Even if the weather seems drab from the foot, driving up to the summit may well lift you above the gray blanket, and the view with a layer of cloud floating between tree line and sky is simply magical.
Mt Greylock State Reservation (park free, summit $2; visitors center 9am–5pm, auto road late May–Oct) has some 45 miles of hiking trails, including a portion of the Appalachian Trail. Frequent trail pull-offs on the road up – including some that lead to waterfalls – make it easy to get at least a little hike in before reaching the top of Mt Greylock.
Return to US 7 and continue north through the quintessential college town of Williamstown. Cross the Vermont border and continue north through the historic village of Bennington. Just north of Bennington, turn left on Rte 7A and continue north to Manchester.
Stylish Manchester is known for its magnificent New England architecture. For fall foliage views, head south of the center to 3828ft-high Mt Equinox (equinoxmountain.com; car & driver $15, each additional passenger $5; 9am–dusk May–Oct), the highest mountain accessible by car in the Taconic Range. Wind up the 5.2 miles – with gasp-inducing scenery at every hairpin turn – seemingly to the top of the world, where the 360-degree panorama unfolds, offering views of the Adirondacks, the lush Battenkill Valley and Montréal’s Mt Royal. If early snow makes Mt Equinox inaccessible, visit 412-acre Hildene, a Georgian Revival mansion that was once home to the Lincoln family. It’s filled with presidential memorabilia and sits nestled at the edge of the Green Mountains, with access to 8 miles of wooded walking trails.
Take US 7 north to Burlington. Three miles past Middlebury in New Haven, stop off at Lincoln Peak Vineyard (lincolnpeakvineyard.com) for wine tasting or a picnic lunch on the wraparound porch.
7. Lake Champlain
With a surface area of 490 sq miles, straddling New York, Vermont and Quebec, Lake Champlain is the largest freshwater lake in the US after the Great Lakes. On its northeastern side, Burlington is a gorgeous base to enjoy the lake. Explore it by foot on our walking tour. Then scoot down to the wooden promenade, take a swing on the fourperson rocking benches and consider a bike ride along the 7.5-mile lakeside bike path.
For the best off-shore foliage views we love the Friend Ship sailboat at Whistling Man Schooner Company (whistlingman.com; College St; 2hr cruise adult/child $40/25; May–Oct), a 43ft sloop that accommodates a mere 17 passengers. Next door, ECHO Lake Aquarium & Science Center (echovermont.org) explores the history and ecosystem of the lake, including a famous snapshot of Champ, Lake Champlain’s mythical sea creature.
Take I-89 southeast to Montpelier passing Camels Hump State Park and CC Putnam State Forest. At Montpelier, pick up US2 heading east to St Johnsbury, where you can hop on I-91 south to I-93 south. Just after Littleton, take US 302 east to Bretton Woods.
8. Bretton Woods
Unbuckle your seat belts and step away from the car. You’re not just peeping at leaves today, you’re swooping past them on zip lines that drop 1000ft at 30mph. The four-season Bretton Woods Canopy Tour (brettonwoods.com; US 302; per person $110; tours 10am & 2pm) includes a hike through the woods, a stroll over sky bridges and a swoosh down 10 cables to tree platforms.
If this leaves you craving even higher views, cross US 302 and drive 6 miles on Base Rd to the coal-burning, steam-powered Mount Washington Cog Railway (thecog.com; adult/child/senior $66/39/59; 8:30am–4:30pm) at the western base of Mt Washington, the highest peak in New England. This historic railway has been hauling sightseers to the mountain’s 6288ft summit since 1869.
Continue driving east on US 302, a route that parallels the Saco River and the Conway Scenic Railroad, traversing Crawford Notch State Park. At the junction of NH 16 and US 302, continue east on US 302 into North Conway.
9. North Conway
Many of the best restaurants, pubs and inns in North Conway come with expansive views of the nearby mountains, making it an ideal place to wrap up a fall foliage road trip. If you’re traveling with kids or you skipped the cog railway ride up Mt Washington, consider an excursion on the antique Valley Train with the Conway Scenic Railroad; it’s a short but sweet roundtrip ride through the Mt Washington Valley from North Conway to Conway, 11 miles south. The Moat Mountains and the Saco River will be your scenic backdrop. First-class seats are usually in a restored Pullman observation car.
This road trip is taken from Lonely Planet's USA's Best Trips guidebook – 52 amazing road trips across America.