15 Century Old Massachusetts Family Restaurants That Still Pack Lines Around the Block

Culinary Destinations
By Lena Hartley

Massachusetts is home to a treasure trove of family-owned restaurants, each steeped in history and tradition. These eateries have not only stood the test of time but also continue to draw crowds with their unique charm and delectable offerings. Here are 15 century-old restaurants that have become beloved institutions in the state.

1. Union Oyster House

© National Trust for Historic Preservation

Nestled in the heart of Boston, Union Oyster House has been serving delicious seafood since 1826. Known for its iconic oysters, the ambiance reflects the rich history of the area. Walking in feels like stepping back in time, with its polished wooden interiors and memorabilia adorning the walls.

The restaurant’s location near the Freedom Trail makes it a popular stop for tourists and locals alike. Its reputation for fresh seafood and historical charm keeps patrons coming back. Whether you’re a fan of clams or chowder, Union Oyster House offers an authentic taste of New England.

Why it still packs: historic ambiance, iconic status, great location.

2. Santarpio’s Pizza

© Framed By History – WordPress.com

Santarpio’s Pizza in East Boston began as a humble bakery in 1903, transitioning to a pizza haven in 1933. This family-owned gem is famous for its Boston-style pies, crafted with a blend of tradition and flavor. The rustic interior adds to the charm.

Loyal patrons and newcomers alike gather for hearty meals and authentic Italian-American classics. Despite the bustling lines, the wait is always worth it. The sense of community and authenticity is palpable, making each visit a memorable experience.

Why it draws: local legend, authenticity, value.

3. Longfellow’s Wayside Inn

© The Boston Globe

Longfellow’s Wayside Inn in Sudbury exudes historic charm. Dating back to pre-colonial times, it’s more than just a restaurant; it’s a step into history. The inn’s atmosphere is steeped in tradition, offering a cozy escape from modern life.

Visitors enjoy traditional New England fare amidst the quaint surroundings. The combination of history and hospitality ensures a steady stream of guests. It’s a popular spot for special occasions, where memories are made against a timeless backdrop.

Why it appeals: unique historic atmosphere, traditional fare.

4. The Federal

© Hartford Courant

Established in 1936, The Federal in Agawam has long been a family operation. The Moretti family’s dedication to quality is evident in every dish. The elegant setting complements their menu of steak, pasta, and seafood.

The blend of traditional and contemporary flavors creates a dining experience to savor. Generational ownership and a strong local reputation keep patrons coming back, ensuring the restaurant’s place in the community.

Why it draws: family ownership, timeless menu, reputation.

5. The 1761 Old Mill

© 1761 Old Mill Restaurant

The 1761 Old Mill in Westminster is a testament to enduring charm. Originally an industrial mill, it was transformed into a restaurant, offering rustic dining with a view. The scenic setting is as much a draw as the menu.

Diners enjoy the blend of history and hospitality, making it a favorite for both locals and tourists. The hearty meals and picturesque environment create a memorable experience, often becoming a family tradition.

Why people go: scenic setting, history, good food.

6. Rye Tavern

© Only In Your State

Rye Tavern in Plymouth stands serenely along Old Sandwich Road. Originally built in 1792, its history is woven into the fabric of the community. The tavern offers a delightful mix of historical ambiance and modern comfort.

Diners are treated to a menu inspired by local ingredients, served in an inviting, rustic setting. The blend of history and culinary excellence makes it a sought-after destination for food enthusiasts.

Why relevant: deep historical roots, destination dining.

7. Salem Cross Inn

© VisitingNewEngland.com

Salem Cross Inn in West Brookfield offers a dining experience steeped in the 1700s. Housed in a colonial farmhouse, it exudes rustic charm, making guests feel miles away from the modern world.

The menu features traditional New England fare, prepared with care and attention to detail. The inn’s historical ambiance and special-occasion value keep guests returning, ensuring its continued legacy.

Why it draws: atmosphere, destination, special-occasion value.

8. Concord’s Colonial Inn

© New England Inns and Resorts

Concord’s Colonial Inn is a historical treasure trove. Established in 1716, it’s woven into the tapestry of Concord’s rich history. The inn offers a charming blend of past and present, attracting history buffs and food lovers alike.

Guests enjoy quality food in a setting that speaks of yesteryears, surrounded by the town’s historic landmarks. The inn’s charm and quality continue to make it a favorite.

Why it draws: historic context, charm, quality food.

9. The Red Lion Inn

© Historic Hotels of America

The Red Lion Inn in Stockbridge has been a beacon of hospitality since 1773. Nestled in the Berkshires, it offers guests an idyllic retreat. The inn exudes warmth with its historic charm and inviting atmosphere.

Known for destination dining, it attracts both visitors and locals. The scenic locale and consistent quality make it a perennial favorite, inviting guests to return year after year.

Why it attracts lines: destination dining, scenic locale.

10. Amrheins Restaurant

© The Boston Globe

Since 1890, Amrheins Restaurant has been a cornerstone of South Boston. Known as the oldest restaurant in the area, it offers a slice of history with every meal. The pub-restaurant vibe is both welcoming and nostalgic.

Serving up classic New England dining, it’s a neighborhood institution where locals gather. The atmosphere is lively, filled with memories and laughter, making every visit special.

Why draws: historic feel, neighborhood institution.

11. The Student Prince Cafe & Fort Dining Room

© Tripadvisor

Opening in 1935, The Student Prince Cafe in Springfield offers a taste of Germany. While not quite a century old, its long-standing tradition and beloved status make it iconic. The decor transports guests to a European beer garden.

Hearty meals and a fun atmosphere keep guests entertained. It’s a perfect spot for celebrations, embodying a spirit of camaraderie and joy.

Why it packs: German decor, hearty meals, fun atmosphere.

12. Warren Tavern

© The Business Journals

Established in 1780, Warren Tavern in Charlestown is one of Massachusetts’ oldest. Though more tavern than restaurant, it serves great food in a historic setting. Its proximity to attractions like Bunker Hill adds appeal.

The tavern’s charm and hearty meals draw both locals and tourists. Conversations echo with stories of the past, making every visit a journey through time.

Why it draws: historic charm, proximity to attractions.

13. Woodman’s of Essex

© Only In Your State

Woodman’s of Essex has been delighting seafood lovers since its founding in 1914. Known for inventing the fried clam, it draws crowds with its iconic dishes. The family-run establishment is quintessentially New England.

Visitors are often greeted with lines, yet the rewarding experience of fresh seafood makes it worthwhile. The casual, welcoming atmosphere resonates with both locals and tourists.

Why it attracts: fried clam origins, seafood reputation.

14. J.J. Foley’s Cafe

© Wheree

J.J. Foley’s Cafe has been a South End institution since 1909. This Irish pub offers classic pub fare with a side of history. The cozy, wood-paneled interior invites guests to relax and enjoy.

Known for its friendly service and hearty meals, it’s a favorite spot for both locals and those exploring Boston. The tradition and sense of community keep patrons returning.

Why it draws: classic pub fare, historic setting.

15. Kowloon Restaurant

© Boston.com

Opened in 1950, Kowloon Restaurant in Saugus offers a unique dining experience. The tiki-themed decor adds flair to its diverse pan-Asian menu, making it a family favorite for generations.

The restaurant is a lively, colorful spot where families gather for celebrations and delicious meals. The tradition and spirited ambiance ensure its continued popularity.

Why it draws: unique theme, diverse menu, family favorite.