Things to Do in Lee, MA: Top Picks

Church and town hall in downtown Lee, down the street from the Lee Library

Yes, Lenox, Massachusetts, is well-known, but don’t overlook Lee, Massachusetts. This New England town, less pretentious yet equally charming, boasts a rich history and plenty of activities. Whether you’re hiking picturesque trails or savouring local cuisine, Lee is a fantastic day trip destination. And it’s an ideal central location to explore everything else in this corner of the Berkshires.

 

Ready to discover the best things to do in Lee, MA? Let’s get into it:

 

Quick hits

  • Discover Lee, MA’s rich history and vibrant present. You’ll find outdoor adventures, cultural attractions, and historic sites galore!
  • Savor the unique flavors at the Farmers Market. For sports enthusiasts, a classic golf course experience awaits at Greenock Country Club.
  • Fancy a road trip? Take a scenic two-hour drive to nearby Lenox. There, you’ll find more attractions and activities such as Edith Wharton’s home and Tanglewood performances.

A Brief History of Lee, Massachusetts

1910 postcard of the post office in downtown Lee

Lee, Massachusetts, was established in 1850. This old mill town features ties to the marble industry. It also has ties to Major-General Charles Lee, a Revolutionary War leader.

 

Originally, Lee was the territory of Mahican Indians. It was incorporated in 1777. The town owes its name to Revolutionary War General Charles Lee. It was once a major industry hub with early industries including agriculture, lumbering, lime making, and papermaking.

 

Industrial Era

The Willow Mill in South Lee was established in 1806. The Columbia Mill in central Lee followed in 1827. By 1857, there were 25 paper mills in Lee. The Smith Paper Company even became the country’s largest producer of paper in the 1870s.

 

1905 photo of a marble quarry in Lee, Massachusetts

Lee is famous for its quality marble. The first quarry was established in 1852. In 1867, almost 500,000 cubic feet of marble was excavated and shipped on the Housatonic Railroad. Buildings constructed from Lee marble include:

 

  • The Capitol in Washington
  • Philadelphia City Hall
  • General Grant National Memorial
  • St. Patrick’s Cathedral in New York City

 

The town’s 19th-century prosperity is reflected in its architecture. It includes the town hall, library, churches, and private homes. South Lee even includes a historic district listed on the National Register.

 

Modern Era

Today, Lee is a popular tourist destination known for its New England charm and bed and breakfasts. It is known as the “Gateway to The Berkshires” as it provides one of only two exits on the Massachusetts Turnpike that serves the county.

 

The Best Things to do in Lee, MA

Town Hall in downtown Lee

Lee, Massachusetts, offers a wide range of activities for all types of travelers. Outdoor enthusiasts will appreciate the town’s proximity to the largest state forest in Massachusetts, October Mountain State Forest. In addition, a variety of Berkshire landmarks are within easy reach. Every September, the town hosts the Festival Latino, a vibrant celebration of Hispanic Heritage Month.

 

So, whether you’re a nature enthusiast, history aficionado, or arts lover, read on for top attractions to explore in Lee, MA.

 

Downtown Lee

The town’s historic downtown area is a sight to behold. It offers a peek into its past while the bustling arts scene highlights its vibrant present.

 

Start your visit with a stroll down Main Street. It’s a great way to soak in the town’s unique atmosphere before diving into the numerous attractions and activities.

 

October Mountain State Forest

October Mountain State Forest

October Mountain State Forest holds the title for the largest state forest in Massachusetts. It boasts:

 

  • Over 100 miles of hiking trails, plus plenty of space for camping, fishing, and hunting

 

  • A vast expanse of 11,000 acres of land that stretches across Washington, Lenox, Lee, and Becket

 

  • A rich history, having been a part of the estate of William C. Whitney, the 31st United States Secretary of the Navy

 

Be prepared for encounters with wildlife such as deer, raccoons, foxes, songbirds, and even black bears on the hiking trails.

 

Santarella

Santarella was designed by Henry Hudson Kitson as his home and studio near Lee, Massachusetts

Have you visited the Santarella Estate in Massachusetts? It’s like a fairy tale. The main attraction is the Tyringham Gingerbread House. This quaint cottage was crafted by Sir Henry Hudson Kitson, an English-born sculptor. He was famous for his detailed statues of American military heroes and generals. He spent 25 years turning this cottage into his personal studio and home.

 

The house is unique. It has beautiful stained glass windows. The roof is a masterpiece. It’s an 80-ton shingle roof, designed to look like the thatched roofs of old English houses. Kitson had a plan to use rye for an authentic thatched roof. However, this plan didn’t work out. Instead, he used hand-cut tiles, layered to create the roof.

 

The Gingerbread House isn’t the only attraction at the Santarella Estate. There’s an old silo that Kitson transformed into another studio. There’s also a cozy cottage that now serves as a bed and breakfast. And the entire estate is surrounded by a lush garden.

 

Lee Library

1909 postcard of the Lee Library, one of the most impressive architectural buildings

Step back in time and visit the historic Lee Library, the only remaining Carnegie library building in the Berkshires. Here, you can:

 

  • Access free WiFi
  • Use computers
  • Book a meeting room
  • Browse an extensive collection of books, magazines, and newspapers.

 

Visit this charming and historic library to get a sense of Lee’s cultural heritage.

 

Lee Farmers Market

Farmers market

For a taste of local flavor, head to the Lee Farmers Market, held every Saturday from 10:00 am to 2:00 pm, rain or shine. From May to October, you can browse a variety of vendors selling:

 

  • fresh produce
  • baked goods
  • honey
  • flowers
  • imported meats, cheeses, and breads
  • unique finds such as goat milk soap, CBD oils, and live lobster tanks

 

Don’t miss the chance to sample all the delicious offerings at the market.

 

You can find the market at 15 Park Place in Lee, MA.

 

Greenock Country Club

Playing a golf course in Massachusetts, one of the best outdoor activities

Golf enthusiasts will love the Greenock Country Club, a public golf club with a 9-hole course, clay tennis courts, and a clubhouse. Established in 1895 and redesigned by Donald Ross in 1927, the club offers a challenging and scenic golf experience.

 

Visit the Greenock Country Club’s website for opening hours and special events, and prepare for a stylish tee off.

 

Goose Pond Reservation

Goose Pond Reservation is a 112-acre wilderness area. It’s managed by the Trustees of Reservations. The reservation can be accessed via a state boat ramp on Ridge Street. Here, you’ll find Lower Goose Pond, a mountain lake surrounded by steep ridgelines. These ridgelines support a remote section of the Appalachian Trail. The lake and the surrounding forest lie next to conservation land. This land is owned by the National Park Service and is crossed by the Appalachian Trail. If you have a canoe or kayak, you can reach the reservation. It’s on the left bank of Lower Goose Pond. However, the rocky and steep shoreline may make landing difficult. The property doesn’t have any formal trails.

 

Sandy Beach at Laurel Lake

lake in Massachusetts

Looking for a place to relax and swim? Sandy Beach at Laurel Lake is just the spot. It offers a public beach with a wide sandy shoreline in a beautiful setting. The beach is open daily from noon until 7 p.m. for Lee residents and homeowners. Visitors can obtain a free beach pass and spend a day sunbathing, swimming, and picnicking on the shores of this picturesque lake.

 

High Lawn Farm

Dairy cows

Visit High Lawn Farm, a working dairy farm and creamery in Lee, for a unique and educational experience. Enjoy hayrides, tours of the dairy barn, and learn how to make ice cream at this charming farm.

 

Don’t miss the opportunity to sample their delicious artisanal cheeses, made on-site using milk from their own Jersey cows.

 

Wineries near Lee, MA

Visiting Wineries near Lee, MA

If you’re a wine enthusiast, be sure to visit the nearby wineries of Balderdash Cellars and Furnace Brook Winery. Balderdash Cellars is a boutique winery in Richmond, Massachusetts, founded by Christian and Donna Hanson. The grounds feature a historic barn on the property.

 

Furnace Brook Winery, located at Hilltop Orchards in Richmond, is just 9.1 miles from Lee and offers wine tours and tastings. Sample local wines and enjoy the beautiful vineyard settings at these nearby wineries.

 

Shopping in Lee, Massachusetts

Shopping Excursion in Lee, Massachusetts

In Lee, you’ll discover a unique blend of shopping experiences. The town hosts a mix of unique boutiques and well-known outlets. Whether you’re on a hunt for unique finds or seeking great deals on popular brands, Lee caters to all types of shoppers. Read one for some of the most unique (or well-known) shops in Lee, MA:

 

Ozzie’s Glass Gallery

For a truly unique shopping experience, visit Ozzie’s Glass Gallery. Here, you’ll find an amazing selection of hand-blown glass art and gifts, including:

  • Jewelry
  • Flower vases
  • Wall hangings
  • Animal sculptures

 

The art gallery also offers live glassblowing demonstrations, allowing you to witness the incredible skill and artistry involved in creating these stunning pieces.

 

Retro Pop Shop

Step back in time at the Retro Pop Shop, where you can browse vintage items and memorabilia in a fun, eclectic setting. Open on Saturdays, Sundays, and Mondays, this unique store offers everything Americana, from:

  • advertising and collectibles
  • American iconic pop items
  • porcelain and tin signs
  • retro roadside memorabilia

 

Lee Premium Outlets

For great deals on popular brands, visit Lee Premium Outlets, a shopping center with over 50 stores. Just a short drive from downtown Lee and conveniently located off the Mass Pike, you’ll find brands like:

  • Aeropostale
  • American Eagle Outfitters
  • Ann Taylor Factory Store
  • Banana Republic Factory Store
  • Bath & Body Works

 

Restaurants in Lee, MA

Dining Delights in Lee, MA

From casual diners to fine dining establishments, Lee offers a variety of delicious dining options to satisfy your taste buds. Whether you’re in the mood for American cuisine, seafood, or a cozy tavern atmosphere, there’s a restaurant in Lee to suit your culinary preferences.

 

Here are some popular local eateries you might want to try, by meal:

 

Lunch, Brunch, & Breakfast in Lee, MA

If you’re planning a day trip up here, be sure to arrive in time for breakfast. Or at least brunch.

 

Starving Artist Creperie and Cafe

Satisfy your cravings for sweet and savory crepes at the Starving Artist Creperie and Cafe in Lee. in Lee. This charming cafe offers an extensive menu of delectable crepes, hot soups, and panini sandwiches.

 

Whether you’re in the mood for a sweet treat or a savory meal, you’ll find something to delight your taste buds at this delightful cafe.

 

Joe’s Diner

Classic diner that still attracts plenty of guests

Experience a classic diner atmosphere at Joe’s Diner, a local favorite in Lee, Massachusetts. Opened in 1955 by Joseph F. Sorrentino, Joe’s Diner offers delicious home-cooked meals, including their signature dishes of:

 

  • Link Sausage
  • French Toast
  • Pancakes
  • Eggs and Toast
  • Corned Beef Hash

 

This iconic diner even served as the inspiration for Norman Rockwell’s famous painting, The Runaway.

 

Dinner in Lee, Massachusetts

Afer a busy day of exploring Lee, you might as well stay for dinner! Some top recommendations include:

 

51 Park Restaurant & Tavern

51 Park Restaurant & Tavern offers a cozy atmosphere for guests to enjoy delicious American cuisine. The menu features:

 

  • Wood-fired pizza
  • Burgers
  • Steak
  • Salmon
  • Mussels
  • Wings
  • Burboli
  • Stromboli
  • Jalapeño poppers

 

With its welcoming ambiance and diverse menu, 51 Park is a great dining destination for locals and visitors alike.

 

Salmon Run Restaurant

a dish at Salmon Run Restaurant

For a taste of the sea, visit Salmon Run Restaurant in Lee, Massachusetts. in Lee, Massachusetts. Offering a menu filled with:

 

  • Fresh seafood catches
  • Juicy steaks
  • Tender chicken
  • Creative pasta dishes

This family-owned and operated restaurant is sure to please seafood lovers and landlubbers alike. Don’t miss their delicious starters like Maryland Crab Cakes and Asian Wings, or their weekend specials like Coconut Shrimp and Slow Roasted Prime Rib.

 

Cafe Triskele

You’ll find a charming bistro on Main Street, Cafe Triskele. Run by a French chef from Brittany and an American pastry chef, this place is all about the passion for cooking and eating well. Their team is small, but talented. They care deeply about the authenticity of their ingredients and the origins of their wines. Attention to detail is their forte, both in preparation and service.

 

Morgan House Inn & Restaurant

Dine on fresh, locally-sourced American cuisine at the historic Morgan House Inn & Restaurant in downtown Lee. in downtown Lee. Located in a beautifully restored building dating back to 1813, the restaurant offers a cozy atmosphere and delicious dishes made from the finest local ingredients.

 

Join the lengthy list of patrons since 1853 that have enjoyed a memorable meal at this charming establishment. And just steps away from Lee’s Main Street.

 

Locker Room Sports Pub

Catch a game and enjoy pub fare at the Locker Room Sports Pub in Lee, Massachusetts. This lively sports bar offers a great atmosphere for watching your favorite teams, along with a menu featuring classic pub favorites.

 

Open Wednesday to Sunday, the Locker Room Sports Pub is the perfect spot to kick back with friends and enjoy a fun night out.

 

Moe’s Tavern

For a laid-back night out, head to Moe’s Tavern in Lee. This popular local tavern offers a relaxed atmosphere, a wide selection of drinks, and live music on weekends.

 

Featuring jazz, rock, blues, and swing music, Moe’s Tavern is a great place to unwind with a drink and enjoy some tunes. And it’s won awards for being the best small town bar in the entire state.

 

Hotels, Inns, and Places to Stay in Lee, Massachusetts

guest room in one of the hidden gems of inns on a Saturday morning

If you’re feeling particularly adventurous (and really love driving), Lee is about a 2 hour, 15 minute day trip from our CT bed and breakfast in Greenwich, Connecticut.

 

But this writer loves the Berkshires. As such, I would never recommend a quick fly-by through the area. And finding perfect accommodations for your visit to Lee is a breeze, with a variety of options to choose from:

 

  • Charming inns
  • Comfortable hotels
  • Elegant country inns
  • Historic bed and breakfasts

 

Whether you prefer the elegance of a country inn, the historic charm of a bed and breakfast, or the convenience of a hotel, there’s a place to stay in Lee that’s just right for you.

 

Lake House Inn

Overlooking Laurel Lake, the Lake House Inn provides a picturesque setting for your stay in Lee. The inn boasts:

  • A private beach
  • Kayaks
  • Paddleboards
  • A swimming pool
  • A hot tub
  • A fitness center
  • A restaurant

 

These amenities perfectly blend modern conveniences with the inn’s historic charm.

 

Chambery Inn

Experience a cozy stay at the historic Chambery Inn, close to Berkshire landmarks in Lee. This charming inn offers:

  • Guest rooms and suites
  • Complimentary breakfast
  • Free Wi-Fi
  • Fitness center

 

The Chambery Inn, with its unique history as a former Roman Catholic elementary school building, provides a memorable backdrop for your visit to Lee. The architectural features of the building add an extra layer of charm to your stay.

 

Devonfield Inn

For a luxurious stay, head to the elegant Devonfield Inn. This English-style country estate is located in the charming town of Lee. Set amidst 32 acres of lush lawns and birch trees, it’s a peaceful retreat. The inn offers spacious rooms, well-appointed with modern amenities. Whether your visit to the Berkshires is for exploration or relaxation, the Devonfield Inn provides the perfect setting for a memorable stay.

 

Federal House Inn

Relax at the charming Federal House Inn, another Berkshires bed and breakfast in Lee, MA. Situated in a beautifully restored building dating back to 1824, this cozy inn offers:

 

  • Comfortable rooms
  • A complimentary breakfast
  • Free Wi-Fi
  • Parking facilities

Experience the warmth and hospitality of this historic inn during your visit to south Lee.

 

Directions to Lee, MA, from Greenwich, CT

For easy weekend getaways from CT, take the scenic Route 7 from Greenwich, CT, to Lee, MA, a journey of just over two hours. With no tolls along the way, you can enjoy a scenic drive through small towns and beautiful landscapes. As you make your way towards Lee, keep an eye out for noteworthy landmarks like:

 

 

More Towns and Cities to Explore Near Lee, Massachusetts

Dirt road leading to an old cemetery in October Mountain State Forest in Lee, MA

While you’re in the area, consider exploring nearby cities and towns in the Berkshires of Massachusetts, for even more attractions and activities. Extend your exploration beyond Lee to fully appreciate the beauty and charm of the Berkshires region.

 

Lenox, MA

In Lenox, MA, you’ll find a wealth of activities and attractions to enjoy during your visit. Just four miles from Lee, Lenox offers attractions like:

 

  • Exploring the historic home of Edith Wharton at The Mount
  • Relaxing at the renowned Canyon Ranch wellness resort
  • Berkshire Scenic Railway Museum
  • Taking in a performance at Tanglewood, the summer home of the Boston Symphony Orchestra

 

Boasting stunning scenery, historical sites, and cultural attractions, Lenox is a must-visit destination in the heart of the Berkshires. That said, it has a reputation for being crazy expensive, verging on chi-chi. So, stay in Lee and drive over.

 

Stockbridge, Massachusetts

Stockbridge, Massachusetts, is a Berkshires’ gem worth exploring. The town is renowned for its well-preserved 19th-century buildings, offering a variety of attractions and activities. You can visit the iconic Norman Rockwell Museum or the beautiful Berkshire Botanical Garden. Whether you are an art enthusiast, a history buff, or a nature lover, Stockbridge, MA, attractions warrant a day trip.

 

Becket, MA

Becket, MA, a delightful town, is just a short drive from Lee. Nestled in the serene beauty of the Berkshires, Becket offers a tranquil retreat away from the hustle and bustle. The town is known for its rich history, stunning landscapes, and cultural attractions. It’s a must-visit destination for nature lovers, history buffs, and culture enthusiasts. You can hike in the scenic Becket Land Trust Historic Quarry or explore the fascinating Jacobs Pillow Dance Festival and Museum.

 

Great Barrington, Massachusetts

Great Barrington, Massachusetts, is a charming town in the Southern Berkshires. It’s celebrated for its cultural richness and natural beauty. The town offers a range of activities for every type of traveler. You can explore the historic Mahaiwe Performing Arts Center or hike the scenic Monument Mountain. The town boasts a diverse culinary scene, featuring farm-to-table dining and international cuisine. Even more of the best things to do in Great Barrington, MA, includes its arts scene and unique boutiques. Its historical significance make it an essential stop in the Berkshires.

 

Tl;dr

Lee, Massachusetts, brims with charm. Its rich history makes it a fascinating place to explore. The town offers a wide range of activities. Nature lovers can revel in the beauty of the October Mountain State Forest. Food enthusiasts can indulge in the town’s delicious local cuisine. History buffs and arts enthusiasts will also find plenty to enjoy. Lee is a destination that guarantees a memorable experience any time of year.

 

Frequently Asked Questions

 

What is Lee Massachusetts known for?

Lee, Massachusetts, is renowned for several key features. It’s home to the popular Lee Premium Outlets, where shoppers can find great deals on major brands. The town is also famous for its high-quality marble, a significant part of its rich history. Lee also embodies classic New England charm, evident in its well-preserved mill town aesthetic. Lastly, it’s adjacent to the traditional county seat, Pittsfield, adding to its cultural significance.

 

What is it like to live in Lee MA?

Living in Lee, Massachusetts, is a delightful experience. The town has a suburban feel and is well-equipped with various amenities. It boasts above-average schools, making it an ideal place for families. The majority of residents are homeowners, adding to the community’s stability. The town’s political views are moderate, appealing to both young professionals and retirees.

 

What is the largest state forest in Massachusetts?

October Mountain State Forest, covering an impressive 16,500 acres, holds the title of Massachusetts’ largest state forest.

 

What are some popular local eateries in Lee, MA?

There are many great places to eat in Lee. Some of the popular local eateries include 51 Park Restaurant & Tavern and Joe’s Diner. For seafood lovers, Salmon Run Restaurant is a great choice. If you’re in the mood for crepes, check out Starving Artist Creperie and Cafe. For a cozy dining atmosphere, you might want to visit Morgan House Inn & Restaurant. If you’re a sports fan, Locker Room Sports Pub could be your spot. For a laid-back night out, Moe’s Tavern is a good choice.

 

What are some noteworthy landmarks on the drive from Greenwich, CT to Lee, MA?

While journeying from Greenwich, CT to Lee, MA, there are several noteworthy landmarks to check out. Explore the quaint towns nestled in the Litchfield Hills along Route 7. And don’t miss the Chester French sculpture garden located in Pittsfield, MA.