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A Scenic 12-Day Drive Around Vermont


Songquan Deng

Vermont is a land of small towns, many of them the embodiment of an idealized New England. Everywhere we journeyed on our drive through the state, we saw evidence of robust industry and ingenuity — those hallmarks of Yankee culture — in the surprising number of craft shops, artist studios, galleries, artisanal cheese producers, stylish restaurants and furniture makers we came across. Vermont also has a varied topography that includes pastoral vistas, forested hills and mountain slopes offering the East’s best skiing. Here is a guide for those who may want to follow in our footsteps.

Our itineraries are for your inspiration. If you do not see specific departure dates listed, please contact Andrew Harper Travel to customize this itinerary to fit your needs.
Highlights

    • Sample local cheeses and spirits
    • Visit the workshops, retail outlet and riverside restaurant of the renowned artisanal glassmaker Simon Pearce
    • Stay at one of the finest hideaways in the country
    • Explore the off-season ski country
    • Enjoy Vermont's lively and delightful dining scene 


Day 1 - 2 : Burlington to Manchester

Pick up a rental car at Burlington International Airport and set off on a counterclockwise route around the state. Due south, the town of Manchester (100 miles) offers a fascinating mix of classic homes plus the historic Hildene estate, once home to Abraham Lincoln’s oldest surviving son, Robert Todd Lincoln. A wealth of retail establishments includes the Orvis flagship store and numerous high-end outlet shops as well as one-of-a-kind galleries and the superb independent Northshire Bookstore. Those interested in fly-fishing will not want to miss the American Museum of Fly Fishing. Near Manchester, the fine cheesemaker Taylor Farm specializes in Gouda cheeses. Stay at the lovely 20-room The Reluctant Panther, which has an excellent restaurant. I also recommend The Copper Grouse at the nearby Taconic Hotel.

Day 3 - 4 : Newfane and the Surrounding Countryside

Leaving Manchester, head east to the little town of Newfane (36 miles), which is just north of the thriving town of Brattleboro, itself a lively place of restaurants, shops and galleries that fill its wealth of old brick buildings. Newfane stands around a classic New England green with a cluster of impressive white buildings that includes an elegant Greek Revival county courthouse, a church of beautiful proportions (topped with a heaven-ascending spire), a meeting hall and the handsome Four Columns Inn, where I suggest you stay for the next two nights. The inn’s tavern is a congenial spot for having drinks, and that should be followed by dinner at the well-regarded restaurant Artisan.

On Day 4, visit the nearby Grafton Village Cheese for an extensive tasting and the nearby Saxtons River Distillery for a sip of its delicious Sapling Maple Liqueur.

Day 5 - 6 : North to Quechee and Woodstock

Head north for the town of Woodstock (68 miles). On the way, visit the lovely town of Quechee and the workshops, retail outlet and riverside restaurant of the renowned artisanal glassmaker Simon Pearce. The restaurant serves fine casual fare with a view of the Ottauquechee River and a quaint covered bridge.

Spend the night at Woodstock Inn & Resort, a landmark hotel that stands on the green of a town often cited as one of the prettiest in the United States. Much of this is due to the Rockefellers, who built the inn and also played a key role in preserving many of the town’s historic structures. The inn offers four dining options, a Robert Trent Jones Sr.-designed golf course, tennis, pools, a gym and spa. Enjoy strolling around the beautiful town and exploring its many shops.

Alternatively, you may decide to stay at Twin Farms, a lavish rural retreat located nine miles north of Woodstock amid meadows and woodlands in an unspoiled valley. Twin Farms is justly regarded as one of the finest hideaways in the country, and guests choose from 20 distinctive lodgings. The restaurant is exceptional; other facilities include a spa, gym and Japanese-style soaking tubs.

Day 7 - 8 : Cheese and distilleries near Warren

From Woodstock, drive north to the town of Warren (49 miles). Stay at The Pitcher Inn, a fine property that I have recommended highly for many years. A dinner at 275 Main, the property’s fine dining room, is invariably a memorable experience.

If at all possible (and the season allows), schedule your trip so you can visit the Saturday Farmers’ Market in Waitsfield (9 miles). There you can enjoy the lively atmosphere and sample some of the fine local products, which include cheese from the Von Trapp Farmstead and spirits from the distilleries of Mad RiverCaledonia and Stonecutter. Look in on some of the charming local shops that feature the art and handicrafts of Vermont. You might want to stay in town for a lovely, simple Italian-style dinner at the rustic Peasant. Or head back to Warren to shop at the distinctive Warren Store, and then cross the street back to The Pitcher Inn for a casual meal in the tavern, Tracks.

Day 9 - 10 : Vermont’s Delightful Ski Country

Heading farther north, make for Stowe (29 miles), one of the great ski regions in the eastern U.S. Along the way, stop at Waterbury Center for tastings from both Cabot, one of the major cheesemakers in Vermont, and Smugglers’ Notch, a small artisanal distillery. In Stowe, the goal is Edson Hill, a small inn close to the famous ski slopes. There, the 23 rooms are divided between the so-called Manor House — with brick walls, gray clapboard siding, white trim and gabled roofs — and four guesthouses situated farther up the hill. Along with a good restaurant, the facilities include a lovely outdoor pool. Numerous trails on the property give both hikers and mountain bikers a wealth of options.

The next day, strike out to explore the off-season ski country, and stop for lunch at Flannel, the restaurant at the recently renovated Topnotch Resort. In the evening, investigate the lively Stowe dining scene, particularly the delightful Plate on Main Street.

The next day, strike out to explore the off-season ski country, and stop for lunch at Flannel, the restaurant at the recently renovated Topnotch Resort. In the evening, investigate the lively Stowe dining scene, particularly the delightful Plate on Main Street.

Day 11 - 12 : The Pleasures of Shelburne and Burlington

Departing Stowe, head west toward Burlington and The Inn at Shelburne Farms (40 miles). This fine old property (once a lavish private home) is part of the Shelburne Farms organization, which is dedicated to the propagation of sustainable agriculture. The grounds provide opportunities for hiking, walking and farm visits. The restaurant is excellent, and much of what appears on the plate comes from the farms.

You would do well to devote a good part of the next day to exploring the Shelburne Museum. The rich, varied holdings concentrate on American crafts, art, furniture and folk art, and the actual buildings themselves are representative of regional styles from times gone by. Head to Burlington for a late-afternoon stroll and some shopping, and then have dinner at the congenial Hen of the Wood restaurant. Thus fortified, prepare for the next day’s journey home.

Day 1 - 2 : Burlington to Manchester

Pick up a rental car at Burlington International Airport and set off on a counterclockwise route around the state. Due south, the town of Manchester (100 miles) offers a fascinating mix of classic homes plus the historic Hildene estate, once home to Abraham Lincoln’s oldest surviving son, Robert Todd Lincoln. A wealth of retail establishments includes the Orvis flagship store and numerous high-end outlet shops as well as one-of-a-kind galleries and the superb independent Northshire Bookstore. Those interested in fly-fishing will not want to miss the American Museum of Fly Fishing. Near Manchester, the fine cheesemaker Taylor Farm specializes in Gouda cheeses. Stay at the lovely 20-room The Reluctant Panther, which has an excellent restaurant. I also recommend The Copper Grouse at the nearby Taconic Hotel.

Day 3 - 4 : Newfane and the Surrounding Countryside

Leaving Manchester, head east to the little town of Newfane (36 miles), which is just north of the thriving town of Brattleboro, itself a lively place of restaurants, shops and galleries that fill its wealth of old brick buildings. Newfane stands around a classic New England green with a cluster of impressive white buildings that includes an elegant Greek Revival county courthouse, a church of beautiful proportions (topped with a heaven-ascending spire), a meeting hall and the handsome Four Columns Inn, where I suggest you stay for the next two nights. The inn’s tavern is a congenial spot for having drinks, and that should be followed by dinner at the well-regarded restaurant Artisan.

On Day 4, visit the nearby Grafton Village Cheese for an extensive tasting and the nearby Saxtons River Distillery for a sip of its delicious Sapling Maple Liqueur.

Day 5 - 6 : North to Quechee and Woodstock

Head north for the town of Woodstock (68 miles). On the way, visit the lovely town of Quechee and the workshops, retail outlet and riverside restaurant of the renowned artisanal glassmaker Simon Pearce. The restaurant serves fine casual fare with a view of the Ottauquechee River and a quaint covered bridge.

Spend the night at Woodstock Inn & Resort, a landmark hotel that stands on the green of a town often cited as one of the prettiest in the United States. Much of this is due to the Rockefellers, who built the inn and also played a key role in preserving many of the town’s historic structures. The inn offers four dining options, a Robert Trent Jones Sr.-designed golf course, tennis, pools, a gym and spa. Enjoy strolling around the beautiful town and exploring its many shops.

Alternatively, you may decide to stay at Twin Farms, a lavish rural retreat located nine miles north of Woodstock amid meadows and woodlands in an unspoiled valley. Twin Farms is justly regarded as one of the finest hideaways in the country, and guests choose from 20 distinctive lodgings. The restaurant is exceptional; other facilities include a spa, gym and Japanese-style soaking tubs.

Day 7 - 8 : Cheese and distilleries near Warren

From Woodstock, drive north to the town of Warren (49 miles). Stay at The Pitcher Inn, a fine property that I have recommended highly for many years. A dinner at 275 Main, the property’s fine dining room, is invariably a memorable experience.

If at all possible (and the season allows), schedule your trip so you can visit the Saturday Farmers’ Market in Waitsfield (9 miles). There you can enjoy the lively atmosphere and sample some of the fine local products, which include cheese from the Von Trapp Farmstead and spirits from the distilleries of Mad RiverCaledonia and Stonecutter. Look in on some of the charming local shops that feature the art and handicrafts of Vermont. You might want to stay in town for a lovely, simple Italian-style dinner at the rustic Peasant. Or head back to Warren to shop at the distinctive Warren Store, and then cross the street back to The Pitcher Inn for a casual meal in the tavern, Tracks.

Day 9 - 10 : Vermont’s Delightful Ski Country

Heading farther north, make for Stowe (29 miles), one of the great ski regions in the eastern U.S. Along the way, stop at Waterbury Center for tastings from both Cabot, one of the major cheesemakers in Vermont, and Smugglers’ Notch, a small artisanal distillery. In Stowe, the goal is Edson Hill, a small inn close to the famous ski slopes. There, the 23 rooms are divided between the so-called Manor House — with brick walls, gray clapboard siding, white trim and gabled roofs — and four guesthouses situated farther up the hill. Along with a good restaurant, the facilities include a lovely outdoor pool. Numerous trails on the property give both hikers and mountain bikers a wealth of options.

The next day, strike out to explore the off-season ski country, and stop for lunch at Flannel, the restaurant at the recently renovated Topnotch Resort. In the evening, investigate the lively Stowe dining scene, particularly the delightful Plate on Main Street.

The next day, strike out to explore the off-season ski country, and stop for lunch at Flannel, the restaurant at the recently renovated Topnotch Resort. In the evening, investigate the lively Stowe dining scene, particularly the delightful Plate on Main Street.

Day 11 - 12 : The Pleasures of Shelburne and Burlington

Departing Stowe, head west toward Burlington and The Inn at Shelburne Farms (40 miles). This fine old property (once a lavish private home) is part of the Shelburne Farms organization, which is dedicated to the propagation of sustainable agriculture. The grounds provide opportunities for hiking, walking and farm visits. The restaurant is excellent, and much of what appears on the plate comes from the farms.

You would do well to devote a good part of the next day to exploring the Shelburne Museum. The rich, varied holdings concentrate on American crafts, art, furniture and folk art, and the actual buildings themselves are representative of regional styles from times gone by. Head to Burlington for a late-afternoon stroll and some shopping, and then have dinner at the congenial Hen of the Wood restaurant. Thus fortified, prepare for the next day’s journey home.

A Scenic 12-Day Drive Around Vermont

Contact an Andrew Harper Travel Advisor to book this itinerary or to customize your own! Call (800) 375-4685 or submit the form below.

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