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Constructive Portrait Drawing


  • Willow Vermont 369 Dover Road South Newfane, VT, 05351 United States (map)

Master expressive portrait drawings

Over three full days of instruction and four nights of accommodation, instructor Oliver Sinn will offer a comprehensive yet accessible experience for artists of all levels, whether you are a beginner looking to explore your creative potential or an experienced artist seeking to refine your techniques. This workshop is designed to meet you where you are on your artistic journey.

The workshop will help you delve into the fundamentals of drawing portraits, focusing on essential knowledge of shapes, planes of heads, anatomy, value rendering, and more through engaging exercises and step-by-step demonstrations from life models. Students will learn the techniques of mastering expressive portrait drawings with vine charcoal and charcoal pencils on drawing papers. 

With his keen eye and constructive critique, Oliver will support you to elevate your portrait drawing skills to new heights.

This workshop is for you if…

  • you admire portraits made by masters of contemporary realism.

  • you want to improve your understanding and ability to render portraits of real people from life.

  • you love Vermont around peak foliage time.

  • staying at a well appointed historic inn is a treat.

  • you enjoy tasty and healthy meals made from scratch.

A journey of creativity and self-discovery

Oliver Sinn's work has been recognized on an international level.

Expert Instruction

One of the highlights of this workshop is the chance to receive personalized teaching and feedback from Oliver Sinn. Oliver has over 25 years of professional teaching experience at the Academy of Art University in San Francisco. The workshop is small, allowing you to work closely with Oliver. He will guide you personally through the process of creating stunning, expressive portrait drawings.

Oliver will give a demonstration and discuss compositional themes and create images through models of light and shapes. The concepts of composition, representation and tonal value will be analyzed in depth.

A revival of skills-based art making

A growing movement is gathering to restore skills-based approaches to the creation of great artworks. Momentum is gathering through the emergence of new art institutions in New York City, Boston Massachusetts, Lyme Connecticut, New Salem Massachusetts, and through our annual invitational exhibit here at Willow. The momentum is, in fact, global; new institutions have emerged over the past several decades all over North America, Europe and many parts of Asia.

What to Expect

18 hours of instruction over three days

18 hours model time over three days

28 hours of studio time

Four nights accommodation

Three meals each full day plus dinner on arrival day and brunch on departure day.

Wine and cheese each afternoon

Evening sauna and fire pit

Scheduled time for sightseeing and excursions

Optional guided hikes; peak foliage comes between late September and mid-October

Fee Options

All options include four nights accommodation and meals, 28 hours studio time, 18 hours model and instructor time, afternoon wine and cheese, and evening sauna and firepit.

  • Main House - double occupancy $1875 per person or single occupancy $3275 per person, inclusive of taxes and fees.

  • Pete Nelson Treehouse - double occupancy $2475 per person or single occupancy $4275 per person, inclusive of taxes and fees.

Refund Policy

We understand that travel plans may change. We offer a number of refund options.

  • Grace Window: Willow offers a full refund minus applicable credit card charges for cancelations made within 24 hours of booking. Credit card charges are 3% for most cards or 4.5% for Amex and are applied by your bank on all transactions, including deposits and refunds. Additional charges may be incurred on international cards.

  • Early Cancelation Window: When you call or email to cancel at least 60 days prior to a retreat, Willow offers a 50% refund of deposit(s).

  • Travel Insurance and Late Cancelations: Our travel insurance partner, ResNexus, offers partial to full refund options right up to the day your retreat starts. Travel insurance must be purchased at booking. If you opt not to purchase travel insurance at booking, refunds are not possible after the early cancelation window closes.

In very rare circumstances—such as a natural disaster or global pandemic—Willow may be required to cancel the retreat. If we cancel the retreat for any reason, you will receive a full refund of all payments made to date.

Materials List

"Drawing the Head for Artists"

"Facial Expressions for Artists"

Extra Soft vine charcoal 6mm or wider (not willow charcoal)

6B "generals" charcoal pencils;

Pad of 18 by 24 inch Strathmore 70 lbs Drawing Paper. Medium Surface;

Pad of 18 by 24 inch smooth newsprint

Drawing board with clips

Some sheets of tracing paper

Sharpie ink marker in black

X-acto knife

Kneaded Eraser

Stabilo #645 and #100 pastel pencils.

1-2 sheets of gray or brown toned drawing papers. 

Personal Items List

Shoes: house slippers, studio shoes, outdoor shoes

Hiking shoes and clothing

Sweater and light jacket - layers!

Flashlight or headlamp for evening walks

Water bottle

The Schedule

Arrival Day

Arrive between 3pm and 5pm. Get settled into your room and gather at 6:30 pm in Willow’s dining room for a welcome dinner.

Full Day Workshops

The instructor will offer instruction and demonstration throughout each day. Structure, form, light and materials will be discussed. Meals will be provided and free time after the afternoon session will allow you and other students to go on self-planned excursions in Southern Vermont (Willow has many recommendations to choose from).

Departure day

Wake up to light breakfast followed by studio time from 10am to 12pm to finish up one or more studies. Head home at 1pm with a renewed focus on drawing the portrait.

Want to stay longer? Extend your stay!

Willow encourages retreat participants who wish to stay in the area longer to book rooms or book the treehouse on nights before and after the retreat at sharply reduced rates. Extended bookings include a hearty continental breakfast. Individual rooms are $150-375/night for up to two people. A discount of 10% applies to bookings of 3 or more nights.

An accomplished instructor

Two of Oliver’s portraits were commissioned by Time Magazine and featured on the cover of their March 2020 “100 Women of the Year” issue.

Drawing from Life

Model time is included

Rooms and Amenities at Willow

Willow provides comfortable overnight accommodations in double occupancy rooms. All rooms have dedicated ensuite or hall baths. We are outfitted with all the comforts of a typical guest house — linens, blowdryers, individually controlled heating and air conditioning. Our mattresses, pillows and furniture are exceptionally comfortable. Our soaps, shampoos, conditioners, and lotions are organic. We support local craftspeople by supplying Willow with handmade and high quality goods — everything from lamps to rugs have been made by hand. You will feel very much at home.

Meals at Willow

Meals are provided throughout the retreat. Our meals are healthy and filling, made of local organic and natural ingredients. Please let us know if you prefer vegetarian or gluten free options. Please let us know if you have any food allergies.

Area Attractions

Willow is located in the foothills of the Green Mountains on 5 acres of open space. The property abuts several hundred acres of woods with hiking trails. The property has a large pond, hillside garden, fire pit, and a large south-facing porch for lounging and gathering.

You will have time for optional area excursions in afternoons and evenings. On request, we would be happy to organize a group excursion. More information on amenities and area attractions is offered on our website.

Meet our cats

Willow is home to two sweet and friendly cats, Bear and Scratch. They love our guests and they absolutely adore being petted. But we ask that guests not pick them up. Too much of that and they will become stressed little souls.

We do our best to keep cats out of the guest rooms so that people with allergies can comfortably stay with us. Please help with this by discouraging the cats from entering or napping in your room.

Traveling to Willow

Willow is located in the beautiful and quintessential village of South Newfane (population 300), a satellite of Newfane (population 1,700). We are located 20 minutes northwest of Brattleboro, 20 minutes northeast of Wilmington, and 20 minutes east of Dover and Mount Snow.

  • By car:

    • From Brattleboro, take Route 30 north about 9 miles. Go left on Depot Road where the West River and Rock River meet; travel 2 miles on Depot Road until you cross a small bridge over the Rock River; go left on Dover Road through the village of Williamsville; after passing through Williamsville you will cross a covered bridge. Willow is exactly 1.2 miles on your left. If you come to a stop sign you have gone 300 feet past our driveway.

    • From Wilmington, take Route 100 north toward West Dover about 3.5 miles. A half mile past the River Valley Market, take a right on East Dover Road; travel 1 mile. Take a right on Dover Hill Road; travel 8 miles on Dover Hill Road and E Dover Road (they are continuous) until you reach a 3-way stop sign in the village of South Newfane. Willow is 300 feet past the stop sign on your right.

  • By train: the daily Amtrak Vermonter stops in Brattleboro as it travels from Washington DC to Montreal and back. You can pick it up in New York, Hartford, Springfield to the south or in Montpelier to the north. Taxis are available in Brattleboro or Willow’s owners will pick you up in Brattleboro on the Vermonter’s arrival at 5pm (note this is after check in time).

  • By plane: Travelers may find Hartford (BDL—64.4 miles, 90 minutes) and Boston (BOS—85.7 miles, 2 hours 20 minutes) to be most convenient. Other nearby airports to check are Rutland VT (RUT, 55 miles, 1 hour 20 minutes), Manchester NH (MHT—85 miles, 2 hours), Albany NY (ALB—73 miles, 1 hour 40 minutes), and Worcester MA (ORH, 81 miles, 1 hour 50 minutes).

A note on driving: We are located in rural Vermont! You may have spotty cell service in areas throughout our area. Be sure to set your GPS before leaving from home. Set it by typing our business name “Willow Vermont Retreat” into your search bar. Please don’t use our address, as most GPS engines get rural addresses wrong. But don’t worry one bit, just remember this: following our guidance will land you safely with us; following Google to our address will lead you 4 miles off target.

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Autumn Respite — Gay and Bi Men’s Gathering (Copy)

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Falling Inward: a Vermont Retreat